DD207378A5 - Verfahren zur herstellung von neuen spiro-derivaten des pyrazolo(1,5-d) (1,2,4)triazin ring-systems - Google Patents

Verfahren zur herstellung von neuen spiro-derivaten des pyrazolo(1,5-d) (1,2,4)triazin ring-systems Download PDF

Info

Publication number: DD207378A5
Authority: DD; German Democratic Republic
Prior art keywords: atoms; group; general formula; hydrogen atom; pyrazolo
Prior art date: 1981-11-18

Application number

DD82244924A

Other languages

German (de)

English (en)

Inventor

Tihanyi

Andrasi

Gal

Sineger

Feher

Original Assignee

Alkaloida Vegyeszeti Gyar

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.)

1981-11-18

Filing date

1982-11-17

Publication date

1984-02-29

1982-11-17 Application filed by Alkaloida Vegyeszeti Gyar filed Critical Alkaloida Vegyeszeti Gyar

1984-02-29 Publication of DD207378A5 publication Critical patent/DD207378A5/de

Links

APRYYMZGRJPHAI-UHFFFAOYSA-N pyrazolo[1,5-d][1,2,4]triazine Chemical group C1=NN=CN2N=CC=C21 APRYYMZGRJPHAI-UHFFFAOYSA-N 0.000 title abstract 2
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 29
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
238000000034 method Methods 0.000 claims abstract description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
239000007795 chemical reaction product Substances 0.000 claims abstract description 4
150000003997 cyclic ketones Chemical class 0.000 claims abstract description 3
-1 4-methyl-phenyl-sulphonyloxy Chemical group 0.000 claims description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 3
FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
230000029936 alkylation Effects 0.000 claims 1
238000005804 alkylation reaction Methods 0.000 claims 1
230000002051 biphasic effect Effects 0.000 claims 1
125000001453 quaternary ammonium group Chemical group 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 6
VWOQOMNXHWAQMJ-UHFFFAOYSA-N 1h-pyrazole-5-carbohydrazide Chemical class NNC(=O)C1=CC=NN1 VWOQOMNXHWAQMJ-UHFFFAOYSA-N 0.000 abstract description 3
230000000694 effects Effects 0.000 abstract description 3
125000003003 spiro group Chemical group 0.000 description 34
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 15
230000008018 melting Effects 0.000 description 12
238000002844 melting Methods 0.000 description 12
239000000243 solution Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
230000000147 hypnotic effect Effects 0.000 description 9
239000003208 petroleum Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 7
229940039412 ketalar Drugs 0.000 description 7
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
230000007958 sleep Effects 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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 4
239000013078 crystal Substances 0.000 description 4
UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 4
229960002456 hexobarbital Drugs 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
238000001914 filtration Methods 0.000 description 3
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000013558 reference substance Substances 0.000 description 3
FYGUBWKMMCWIKB-UHFFFAOYSA-N spiro[2.3]hexane Chemical compound C1CC11CCC1 FYGUBWKMMCWIKB-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
KMLPEYHLAKSCGX-UHFFFAOYSA-N 2-aminocyclohexan-1-one Chemical compound NC1CCCCC1=O KMLPEYHLAKSCGX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
241000700159 Rattus Species 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
238000000926 separation method Methods 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
231100001274 therapeutic index Toxicity 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
LWXRVGSVNXASAD-UHFFFAOYSA-N 2-(methylamino)cyclohexan-1-one Chemical compound CNC1CCCCC1=O LWXRVGSVNXASAD-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
VSWQDKUTTXAYKT-UHFFFAOYSA-N 5-hex-1-enyl-5-methyl-1,3-diazinane-2,4,6-trione Chemical compound CCCCC=CC1(C)C(=O)NC(=O)NC1=O VSWQDKUTTXAYKT-UHFFFAOYSA-N 0.000 description 1
VKPLFHKPHXHCEQ-UHFFFAOYSA-N 5H-triazin-4-one Chemical compound N=1N=NC(CC=1)=O VKPLFHKPHXHCEQ-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000008096 xylene 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
- C07D487/10—Spiro-condensed systems
- 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
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Surgery (AREA)
Anesthesiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD82244924A 1981-11-18 1982-11-17 Verfahren zur herstellung von neuen spiro-derivaten des pyrazolo(1,5-d) (1,2,4)triazin ring-systems DD207378A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU813445A HU187474B (en)	1981-11-18	1981-11-18	Process for producing new spiro-pyrazole-square bracket-1,5-d-square bracket closed-square bracket-1,2,4-square bracket closed-triazine derivatives

Publications (1)

Publication Number	Publication Date
DD207378A5 true DD207378A5 (de)	1984-02-29

Family

ID=10964053

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD82244924A DD207378A5 (de)	1981-11-18	1982-11-17	Verfahren zur herstellung von neuen spiro-derivaten des pyrazolo(1,5-d) (1,2,4)triazin ring-systems

Country Status (13)

Country	Link
US (1)	US4469692A (cs)
JP (1)	JPS58135888A (cs)
BE (1)	BE895039A (cs)
BG (1)	BG38788A3 (cs)
CH (1)	CH652721A5 (cs)
CS (1)	CS244916B2 (cs)
DD (1)	DD207378A5 (cs)
DE (1)	DE3242610A1 (cs)
FR (1)	FR2516513B1 (cs)
GB (1)	GB2111487B (cs)
HU (1)	HU187474B (cs)
IT (1)	IT1191084B (cs)
SU (1)	SU1169539A3 (cs)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE791025A (fr) *	1971-11-19	1973-05-07	Allen & Hanburys Ltd	Composes heterocycliques
US4115572A (en) *	1977-02-03	1978-09-19	American Cyanamid Company	Imidazo-[1,5-d]-as-triazin-1(2H)-ones and method of ameliorating asthma
US4168964A (en) *	1977-10-18	1979-09-25	American Cyanamid Company	Method for the control of undesired plant species using imidazo-as-triazinones and triazine-thiones

1981
- 1981-11-18 HU HU813445A patent/HU187474B/hu not_active IP Right Cessation
1982
- 1982-11-09 GB GB08231973A patent/GB2111487B/en not_active Expired
- 1982-11-17 DD DD82244924A patent/DD207378A5/de unknown
- 1982-11-17 US US06/442,451 patent/US4469692A/en not_active Expired - Fee Related
- 1982-11-17 CH CH6697/82A patent/CH652721A5/de not_active IP Right Cessation
- 1982-11-17 BE BE1/10647A patent/BE895039A/fr not_active IP Right Cessation
- 1982-11-17 FR FR8219224A patent/FR2516513B1/fr not_active Expired
- 1982-11-17 CS CS828189A patent/CS244916B2/cs unknown
- 1982-11-17 IT IT8224281A patent/IT1191084B/it active
- 1982-11-18 BG BG058644A patent/BG38788A3/xx unknown
- 1982-11-18 SU SU823519899A patent/SU1169539A3/ru active
- 1982-11-18 JP JP57202838A patent/JPS58135888A/ja active Pending
- 1982-11-18 DE DE19823242610 patent/DE3242610A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
DE3242610A1 (de)	1983-05-26
SU1169539A3 (ru)	1985-07-23
GB2111487B (en)	1985-03-20
IT8224281A1 (it)	1984-05-17
BG38788A3 (en)	1986-02-28
HU187474B (en)	1986-01-28
IT1191084B (it)	1988-02-24
FR2516513B1 (fr)	1986-02-07
CH652721A5 (de)	1985-11-29
JPS58135888A (ja)	1983-08-12
GB2111487A (en)	1983-07-06
US4469692A (en)	1984-09-04
IT8224281A0 (it)	1982-11-17
CS244916B2 (en)	1986-08-14
FR2516513A1 (fr)	1983-05-20
BE895039A (fr)	1983-05-17

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