CA1040631A - 1-nitrophenyl pyrido(2,3-d) pyrimidine-2,4 (1h,3h)-diones - Google Patents

1-nitrophenyl pyrido(2,3-d) pyrimidine-2,4 (1h,3h)-diones

Info

Publication number: CA1040631A
Authority: CA; Canada
Prior art keywords: substituted; lower alkylamino; lower alkyl; alkylamino; compounds
Prior art date: 1974-03-23
Legal status (The legal status 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 status listed.): Expired

Application number

CA220,795A

Other languages

English (en)

Other versions

CA220795S (en

Inventor

Toshiharu Motomura

Kanji Noda

Akira Nakagawa

Hiroyuki Ide

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hisamitsu Pharmaceutical Co Inc

Original Assignee

Hisamitsu Pharmaceutical Co Inc

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.)

1974-03-23

Filing date

1975-02-24

Publication date

1978-10-17

1974-03-23 Priority claimed from JP49032752A external-priority patent/JPS593479B2/ja

1974-04-04 Priority claimed from JP49038978A external-priority patent/JPS582953B2/ja

1975-02-24 Application filed by Hisamitsu Pharmaceutical Co Inc filed Critical Hisamitsu Pharmaceutical Co Inc

1978-10-17 Application granted granted Critical

1978-10-17 Publication of CA1040631A publication Critical patent/CA1040631A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 4
UYBULCLJEWQLKE-UHFFFAOYSA-N 1-(1-nitrocyclohexa-2,4-dien-1-yl)pyrido[2,3-d]pyrimidine-2,4-dione Chemical class C12=NC=CC=C2C(=O)NC(=O)N1C1([N+](=O)[O-])CC=CC=C1 UYBULCLJEWQLKE-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 26
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract 2
125000003282 alkyl amino group Chemical group 0.000 claims description 15
-1 vinyloxyethyl Chemical group 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000004953 trihalomethyl group Chemical group 0.000 claims description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 1
125000004385 trihaloalkyl group Chemical group 0.000 claims 1
230000000202 analgesic effect Effects 0.000 abstract description 9
238000000034 method Methods 0.000 abstract description 9
230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
230000003001 depressive effect Effects 0.000 abstract description 5
210000003169 central nervous system Anatomy 0.000 abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
229940035676 analgesics Drugs 0.000 abstract description 2
230000001387 anti-histamine Effects 0.000 abstract description 2
239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
230000001754 anti-pyretic effect Effects 0.000 abstract description 2
230000000767 anti-ulcer Effects 0.000 abstract description 2
239000000739 antihistaminic agent Substances 0.000 abstract description 2
239000002221 antipyretic Substances 0.000 abstract description 2
125000003710 aryl alkyl group Chemical group 0.000 abstract description 2
239000003874 central nervous system depressant Substances 0.000 abstract description 2
230000000144 pharmacologic effect Effects 0.000 abstract description 2
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 15
239000000203 mixture Substances 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
239000012312 sodium hydride Substances 0.000 description 9
239000012043 crude product Substances 0.000 description 8
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
235000013350 formula milk Nutrition 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
235000005152 nicotinamide Nutrition 0.000 description 5
239000011570 nicotinamide Substances 0.000 description 5
229960003966 nicotinamide Drugs 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
230000001154 acute effect Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
XBLVHTDFJBKJLG-UHFFFAOYSA-N Ethyl nicotinate Chemical compound CCOC(=O)C1=CC=CN=C1 XBLVHTDFJBKJLG-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
230000007059 acute toxicity Effects 0.000 description 3
231100000403 acute toxicity Toxicity 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
TUMNHQRORINJKE-UHFFFAOYSA-N 1,1-diethylurea Chemical compound CCN(CC)C(N)=O TUMNHQRORINJKE-UHFFFAOYSA-N 0.000 description 2
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
230000008034 disappearance Effects 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
GTOKAWYXANYGFG-UHFFFAOYSA-N ethyl n-propylcarbamate Chemical compound CCCNC(=O)OCC GTOKAWYXANYGFG-UHFFFAOYSA-N 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000028527 righting reflex Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
UUMMTMQODCACRH-UHFFFAOYSA-N 2-anilinopyridine-3-carboxylic acid Chemical class OC(=O)C1=CC=CN=C1NC1=CC=CC=C1 UUMMTMQODCACRH-UHFFFAOYSA-N 0.000 description 1
WOBKHHIDUYDHKI-UHFFFAOYSA-N 3-(chloromethyl)-n-phenylpyridin-2-amine Chemical class ClCC1=CC=CN=C1NC1=CC=CC=C1 WOBKHHIDUYDHKI-UHFFFAOYSA-N 0.000 description 1
RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
JEYCTXHKTXCGPB-UHFFFAOYSA-N Methaqualone Chemical compound CC1=CC=CC=C1N1C(=O)C2=CC=CC=C2N=C1C JEYCTXHKTXCGPB-UHFFFAOYSA-N 0.000 description 1
XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
206010029216 Nervousness Diseases 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229960000212 aminophenazone Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
MTMNJFGEKOYMIV-UHFFFAOYSA-N carbonyl dichloride;toluene Chemical compound ClC(Cl)=O.CC1=CC=CC=C1 MTMNJFGEKOYMIV-UHFFFAOYSA-N 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
YICRPEGTQDSFEX-UHFFFAOYSA-N ethyl imidazole-1-carboxylate Chemical compound CCOC(=O)N1C=CN=C1 YICRPEGTQDSFEX-UHFFFAOYSA-N 0.000 description 1
GZXSDYYWLZERLF-UHFFFAOYSA-N ethyl n-ethylcarbamate Chemical compound CCNC(=O)OCC GZXSDYYWLZERLF-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
229940090044 injection Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910000765 intermetallic Inorganic materials 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229960002803 methaqualone Drugs 0.000 description 1
SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 description 1
XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000001379 nervous effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
239000008215 water for injection Substances 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA220,795A 1974-03-23 1975-02-24 1-nitrophenyl pyrido(2,3-d) pyrimidine-2,4 (1h,3h)-diones Expired CA1040631A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP49032752A JPS593479B2 (ja)	1974-03-23	1974-03-23	シンキナピリドピリミジンジオンユウドウタイノセイゾウホウ
JP49038978A JPS582953B2 (ja)	1974-04-04	1974-04-04	シンキナピリドピリミジンジオンユウドウタイノセイゾウホウ

Publications (1)

Publication Number	Publication Date
CA1040631A true CA1040631A (fr)	1978-10-17

Family

ID=26371332

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA220,795A Expired CA1040631A (fr)	1974-03-23	1975-02-24	1-nitrophenyl pyrido(2,3-d) pyrimidine-2,4 (1h,3h)-diones

Country Status (3)

Country	Link
CA (1)	CA1040631A (fr)
CH (1)	CH605945A5 (fr)
SE (1)	SE425247B (fr)

1975
- 1975-02-10 SE SE7501430A patent/SE425247B/xx unknown
- 1975-02-24 CA CA220,795A patent/CA1040631A/fr not_active Expired
- 1975-02-25 CH CH237075A patent/CH605945A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
CH605945A5 (en)	1978-10-13
SE7501430L (fr)	1975-09-24
SE425247B (sv)	1982-09-13

Publication	Publication Date	Title
US3594480A (en)	1971-07-20	Nitrogen heterocycles for therapeutic administration
US3812127A (en)	1974-05-21	4-(quinolin-4-yl)piperazine-1-carboxylic acid esters
US3862143A (en)	1975-01-21	Substituted chromone-3-carbonitriles, carboxamides and carboxylic acids
US3517005A (en)	1970-06-23	Certain 2- and 4-substituted quinazolines
US5719279A (en)	1998-02-17	Asymmetrically substituted xanthines
EP0260817A1 (fr)	1988-03-23	Quinazolinediones et pyridopyrimidinediones
CZ342595A3 (en)	1996-08-14	Purine derivatives, process of their preparation and pharmaceutical compositions containing thereof
CA1175432A (fr)	1984-10-02	Procede d'obtention de derives de n-oxacyclyl- alkylpiperidine; produits pharmaceutiques qui en contiennent et leur emploi
DD258229A5 (de)	1988-07-13	Verfahren zur herstellung von neuen heterocyclisch substituierten indolderivaten
EP0263352A1 (fr)	1988-04-13	Imidazo-benzoxazinones, leur préparation et médicaments contenant ces composés
DE2334266A1 (de)	1974-01-31	Pyrido eckige klammer auf 2,3-d eckige klammer zu pyrimidin-2,4 (1h, 3h)-dione
DD253620A5 (de)	1988-01-27	Verfahren zur herstellung von pyrrolo-benzimidazolen
DD267047A5 (de)	1989-04-19	Verfahren zur herstellung von pyrrolobenzimidazolen
CA1054600A (fr)	1979-05-15	Derives amino d'imidazo (4,5-b) pyridines
US3538086A (en)	1970-11-03	4-oxo-4h-pyrimido 2,1-b benzothiazoles
US4472400A (en)	1984-09-18	Triazoloquinazolones having antihistaminic and bronchospasmolytic activity
US3673188A (en)	1972-06-27	Heterocyclic amidoximes
CA1040631A (fr)	1978-10-17	1-nitrophenyl pyrido(2,3-d) pyrimidine-2,4 (1h,3h)-diones
US3424758A (en)	1969-01-28	Carboalkoyphenoxy and carboalkoxy-phenylmercapto-4-nitropyrazoles
US3627766A (en)	1971-12-14	5,6,7,8-TETRAHYDRO-PYRIDO{8 4{40 ,3{40 :4,5{9 THIENO{8 2,3-d{9 PYRIMIDINES
JPS6026115B2 (ja)	1985-06-21	オキサジアゾロピリミジン誘導体
US3452026A (en)	1969-06-24	Substituted 1,2,3,4-tetrahydroquinolines
US3530140A (en)	1970-09-22	Certain pyridyl-hydrazino-2-yl-imidazolines
US4009166A (en)	1977-02-22	Pyrido(2,3-d) pyrimidinones
US3793326A (en)	1974-02-19	3,4-dihydro-6,7-substituted-2,2,3-lower alkyl-4-oxo-(2h)-quinazolecarboxylic acid derivatives useful as analgesic and tranquilizer agents