SU509227A3 - Способ получени производныхпиримидо (5,4- )пиримидина - Google Patents

Способ получени производныхпиримидо (5,4- )пиримидина

Info

Publication number: SU509227A3
Authority: SU; USSR - Soviet Union
Prior art keywords: bis; pyrimidine; pyrimido; carbon atoms; radical
Prior art date: 1973-01-08

Application number

SU1980992A

Other languages

English (en)

Russian (ru)

Inventor

Рох Йосеф

Кадатц Рудольф

Ириг Ганнс

Original Assignee

Д-Р Карл Томэ Гмбх (Фирма)

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.)

1973-01-08

Filing date

1973-12-27

Publication date

1976-03-30

1973-12-27 Application filed by Д-Р Карл Томэ Гмбх (Фирма) filed Critical Д-Р Карл Томэ Гмбх (Фирма)

1976-03-30 Application granted granted Critical

1976-03-30 Publication of SU509227A3 publication Critical patent/SU509227A3/ru

Links

238000000034 method Methods 0.000 title claims description 7
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title description 6
-1 chlorosulfonyl Chemical group 0.000 claims description 21
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 7
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
238000011835 investigation Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
FRGGNTDUBQNZBA-UHFFFAOYSA-N 2-(2-methoxyethylamino)ethanol Chemical compound COCCNCCO FRGGNTDUBQNZBA-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
238000000746 purification Methods 0.000 description 8
JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical compound N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
238000010438 heat treatment Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
239000002253 acid Substances 0.000 description 4
TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
CWOJDGJXXFBXHO-UHFFFAOYSA-N benzene;ethanol;propan-2-one Chemical compound CCO.CC(C)=O.C1=CC=CC=C1 CWOJDGJXXFBXHO-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000003993 interaction Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
WMTQTMOUNYSPCJ-UHFFFAOYSA-N 2-(3-ethoxypropylamino)ethanol Chemical compound CCOCCCNCCO WMTQTMOUNYSPCJ-UHFFFAOYSA-N 0.000 description 1
GYCQECJYBJUVBE-UHFFFAOYSA-N 2-chloro-4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-6-sulfonyl chloride Chemical compound ClC=1N=C(C2=C(N1)C(=NC(=N2)S(=O)(=O)Cl)N2CCCCC2)N2CCCCC2 GYCQECJYBJUVBE-UHFFFAOYSA-N 0.000 description 1
WONYMNWUJVKVII-UHFFFAOYSA-N 3,5-diiodothyropropionic acid Chemical compound IC1=CC(CCC(=O)O)=CC(I)=C1OC1=CC=C(O)C=C1 WONYMNWUJVKVII-UHFFFAOYSA-N 0.000 description 1
DENIBZMGTUCCSK-UHFFFAOYSA-N 3-(2-methoxyethylamino)propan-1-ol Chemical compound COCCNCCCO DENIBZMGTUCCSK-UHFFFAOYSA-N 0.000 description 1
LESOEEAEULASOJ-UHFFFAOYSA-N 4,8-di(piperidin-1-yl)pyrimido[5,4-d]pyrimidine-2,6-disulfonyl chloride Chemical compound C=12N=C(S(Cl)(=O)=O)N=C(N3CCCCC3)C2=NC(S(=O)(=O)Cl)=NC=1N1CCCCC1 LESOEEAEULASOJ-UHFFFAOYSA-N 0.000 description 1
IWUCSDJZMNVZRU-UHFFFAOYSA-N C(C)S(=O)(=O)C=1N=C(C2=C(N1)C(=NC(=N2)S(=O)(=O)CC)N(CC)CC)N(CC)CC Chemical compound C(C)S(=O)(=O)C=1N=C(C2=C(N1)C(=NC(=N2)S(=O)(=O)CC)N(CC)CC)N(CC)CC IWUCSDJZMNVZRU-UHFFFAOYSA-N 0.000 description 1
HZHZSUPTLVMLAU-UHFFFAOYSA-N C(C)S(=O)(=O)C=1N=C(C2=C(N1)C(=NC(=N2)S(=O)(=O)CC)N2CCCCC2)N2CCCCC2 Chemical compound C(C)S(=O)(=O)C=1N=C(C2=C(N1)C(=NC(=N2)S(=O)(=O)CC)N2CCCCC2)N2CCCCC2 HZHZSUPTLVMLAU-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
239000012043 crude product Substances 0.000 description 1
JMVIPXWCEHBYAH-UHFFFAOYSA-N cyclohexanone;ethyl acetate Chemical compound CCOC(C)=O.O=C1CCCCC1 JMVIPXWCEHBYAH-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 1
125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
239000010408 film Substances 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
VGEMYWDUTPQWBN-UHFFFAOYSA-N n-ethyl-2-methoxyethanamine Chemical compound CCNCCOC VGEMYWDUTPQWBN-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000010409 thin film Substances 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
238000005406 washing Methods 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SU1980992A 1973-01-08 1973-12-27 Способ получени производныхпиримидо (5,4- )пиримидина SU509227A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2300661A DE2300661C3 (de)	1973-01-08	1973-01-08	Pyrimido [5,4-d] pyrimidine, deren physiologisch verträgliche Säureadditionssalze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel

Publications (1)

Publication Number	Publication Date
SU509227A3 true SU509227A3 (ru)	1976-03-30

Family

ID=5868472

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1980992A SU509227A3 (ru)	1973-01-08	1973-12-27	Способ получени производныхпиримидо (5,4- )пиримидина

Country Status (21)

Country	Link
JP (1)	JPS4995996A (fr)
KR (1)	KR780000136B1 (fr)
AT (1)	AT334378B (fr)
BE (1)	BE809474A (fr)
BG (1)	BG25987A3 (fr)
CH (1)	CH590285A5 (fr)
DD (1)	DD110496A5 (fr)
DE (1)	DE2300661C3 (fr)
DK (1)	DK133300C (fr)
ES (1)	ES421810A1 (fr)
FR (1)	FR2213066B1 (fr)
GB (1)	GB1432731A (fr)
HU (1)	HU166653B (fr)
IE (1)	IE38725B1 (fr)
IL (1)	IL43967A (fr)
NL (1)	NL7400100A (fr)
PH (1)	PH9640A (fr)
PL (1)	PL91246B1 (fr)
RO (1)	RO63660A (fr)
SU (1)	SU509227A3 (fr)
ZA (1)	ZA7493B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4388318A (en) *	1981-09-29	1983-06-14	Boehringer Ingelheim International Gmbh	Method of treating endotoxin shock with a pyrimido-pyrimidine derivative
US4963541A (en) *	1989-02-22	1990-10-16	Abbott Laboratories	Pyrimido-pyrimidine lipoxygenase inhibiting compounds

1973
- 1973-01-08 DE DE2300661A patent/DE2300661C3/de not_active Expired
- 1973-12-10 AT AT1028473A patent/AT334378B/de active
- 1973-12-17 BG BG025269A patent/BG25987A3/xx unknown
- 1973-12-27 JP JP49004765A patent/JPS4995996A/ja active Pending
- 1973-12-27 SU SU1980992A patent/SU509227A3/ru active
- 1973-12-27 ES ES421810A patent/ES421810A1/es not_active Expired
- 1973-12-31 KR KR7302360A patent/KR780000136B1/ko not_active Expired
1974
- 1974-01-04 CH CH8274A patent/CH590285A5/xx not_active IP Right Cessation
- 1974-01-04 NL NL7400100A patent/NL7400100A/xx not_active Application Discontinuation
- 1974-01-04 DD DD175839A patent/DD110496A5/xx unknown
- 1974-01-05 RO RO197477199A patent/RO63660A/fr unknown
- 1974-01-07 ZA ZA00740093A patent/ZA7493B/xx unknown
- 1974-01-07 IL IL43967A patent/IL43967A/en unknown
- 1974-01-07 BE BE139590A patent/BE809474A/fr unknown
- 1974-01-07 HU HUTO950A patent/HU166653B/hu unknown
- 1974-01-07 PL PL1974167952A patent/PL91246B1/pl unknown
- 1974-01-07 DK DK7474*#A patent/DK133300C/da active
- 1974-01-07 GB GB58674A patent/GB1432731A/en not_active Expired
- 1974-01-08 PH PH15387*UA patent/PH9640A/en unknown
- 1974-01-08 FR FR7400569A patent/FR2213066B1/fr not_active Expired
- 1974-01-08 IE IE41/74A patent/IE38725B1/xx unknown

Also Published As

Publication number	Publication date
BG25987A3 (bg)	1979-01-12
IE38725B1 (en)	1978-05-24
HU166653B (fr)	1975-04-28
IL43967A (en)	1977-05-31
GB1432731A (en)	1976-04-22
DK133300B (da)	1976-04-26
DE2300661A1 (de)	1974-07-18
KR780000136B1 (en)	1978-04-25
DE2300661C3 (de)	1979-10-31
FR2213066A1 (fr)	1974-08-02
AT334378B (de)	1976-01-10
PH9640A (en)	1976-01-26
JPS4995996A (fr)	1974-09-11
DE2300661B2 (de)	1979-03-08
FR2213066B1 (fr)	1977-09-02
ATA1028473A (de)	1976-05-15
ZA7493B (en)	1975-09-24
IE38725L (en)	1974-07-08
DD110496A5 (fr)	1974-12-20
DK133300C (da)	1976-09-27
BE809474A (fr)	1974-07-08
RO63660A (fr)	1978-12-15
CH590285A5 (fr)	1977-07-29
ES421810A1 (es)	1976-04-16
PL91246B1 (fr)	1977-02-28
NL7400100A (fr)	1974-07-10
IL43967A0 (en)	1974-05-16

Publication	Publication Date	Title
Krutak et al.	1979	Chemistry of ethenesulfonyl fluoride. Fluorosulfonylethylation of organic compounds
AU717569B2 (en)	2000-03-30	Fluorinated xanthene derivatives
JP2740321B2 (ja)	1998-04-15	新規の多官能α−ジアゾーβ−ケトエステル、それらの製法および用途
Kumamoto et al.	1972	Sulfenylation of active methylene compounds with sulfenamides
GB2209751A (en)	1989-05-24	Water-soluble photochromic compounds
SE439307B (sv)	1985-06-10	Mellanprodukter for framstellning av pyrimido(6,1-a)isokinolin-4-on-derivat och forfarande for framstellning av mellanprodukterna
Bell et al.	1975	Synthesis of substituted 3‐amino [6, 5‐b] triazinoindoles
SU509227A3 (ru)	1976-03-30	Способ получени производныхпиримидо (5,4- )пиримидина
Ojima et al.	1973	Reactions of Diphenylphosphinothioyl Isothiocyanate and Related Compounds with Some Nucleophiles and Carbodiimides
Taylor et al.	1978	Pteridines. 43. A facile synthesis of 6-chloropterin and 2, 4-diamino-6-chloropteridine
Hall et al.	1966	Synthesis and Thermal Stability of 1, 2-Diazetidinones. Reaction of Diphenylketene with Substituted Azobenzenes1a
US4286093A (en)	1981-08-25	9-Cyclohexyl-2-alkoxy-9H-adenine process
US3974180A (en)	1976-08-10	Furanes, their manufacture and use
SU561513A3 (ru)	1977-06-05	Способ получени производных пиперазина или их солей
SU1004426A1 (ru)	1983-03-15	Способ получени монометинцианиновых красителей р да 1,3-диметил-1,3-дигидропиримидона-2
Reynolds et al.	1963	Polynuclear Heterocycles. VIII. N-(2-Arylamino-1, 4-dioxynaphthyl-3) pyridinium Salts
Endo et al.	1975	A FACILE SYNTHESIS OF UNSYMMETRICAL DISULFIDES
US3597444A (en)	1971-08-03	Method of synthesizing selenoureas from thioureas
US4837350A (en)	1989-06-06	Process for the preparation of benzoin sulfonates
SU1366517A1 (ru)	1988-01-15	Способ получени 3-( @ -D-глюкопиранозил)-4-оксигексагидропиримидин-2-тиона
Baker et al.	1966	Synthesis of 6‐substituted pyrimidines by the wittig reaction. II. Via 2‐acetamido‐4‐hydroxy‐5‐phenylbutylpyrimidine‐6‐carboxaldehyde
US4332950A (en)	1982-06-01	Thiazolidine-substituted phenyl sulfonic acids
HU182272B (en)	1983-12-28	Process for preparing rhanitidine
US4057562A (en)	1977-11-08	Certain naphthofurans and method for their manufacture
RU2096408C1 (ru)	1997-11-20	Способ получения замещенных амино-1,3,5-триазинов