DD296930A5 - Dihydro-pyrimido-thiazin-derivate und verfahren zu ihrer herstellung - Google Patents
Dihydro-pyrimido-thiazin-derivate und verfahren zu ihrer herstellung Download PDFInfo
- Publication number
- DD296930A5 DD296930A5 DD90342877A DD34287790A DD296930A5 DD 296930 A5 DD296930 A5 DD 296930A5 DD 90342877 A DD90342877 A DD 90342877A DD 34287790 A DD34287790 A DD 34287790A DD 296930 A5 DD296930 A5 DD 296930A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- mol
- methyl
- alkyl
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- -1 nitro, amino Chemical group 0.000 claims abstract description 55
- 238000002360 preparation method Methods 0.000 claims abstract description 55
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
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- 230000003110 anti-inflammatory effect Effects 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 230000008569 process Effects 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 82
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 23
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
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- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000002870 angiogenesis inducing agent Substances 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000002973 irritant agent Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004899 motility Effects 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
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 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
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000004622 sleep time Effects 0.000 description 1
- 230000036578 sleeping time Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Luminescent Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU893658A HU203878B (en) | 1989-07-19 | 1989-07-19 | Process for producing tetrahydro-pyrimidine carboxylic acid derivatives |
| HU365989A HU205123B (en) | 1989-07-19 | 1989-07-19 | Process for producing dihydropyrimidino thiazine derivatives and pharmaceutical compositions comprising same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD296930A5 true DD296930A5 (de) | 1991-12-19 |
Family
ID=26317670
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD90342877A DD296930A5 (de) | 1989-07-19 | 1990-07-18 | Dihydro-pyrimido-thiazin-derivate und verfahren zu ihrer herstellung |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5071849A (cs) |
| EP (1) | EP0409223A3 (cs) |
| JP (1) | JPH03148284A (cs) |
| KR (1) | KR940006637B1 (cs) |
| AT (1) | AT399879B (cs) |
| BE (1) | BE1004489A3 (cs) |
| BG (1) | BG60209B2 (cs) |
| CA (1) | CA2021556A1 (cs) |
| CZ (1) | CZ280445B6 (cs) |
| DD (1) | DD296930A5 (cs) |
| ES (1) | ES2027492A6 (cs) |
| FR (1) | FR2649981B1 (cs) |
| GB (1) | GB2234508B (cs) |
| GR (1) | GR910300031T1 (cs) |
| HU (1) | HU203878B (cs) |
| IL (1) | IL95091A (cs) |
| IT (1) | IT1249212B (cs) |
| PL (1) | PL163653B1 (cs) |
| RU (1) | RU2022965C1 (cs) |
| YU (1) | YU47949B (cs) |
| ZA (1) | ZA905456B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5677300A (en) * | 1993-03-29 | 1997-10-14 | The Green Cross Corporation | Pyridothiazineacetic acid compound, production thereof and use thereof |
| RU2169732C1 (ru) * | 1997-04-02 | 2001-06-27 | Ашкинази Римма Ильинична | Производные 5-оксо-5н-[1]-бензопирано-[5,6-b]4-оксо-4н-[1,2]-пиримидо-1,4,5,6-тетрагид ро-1,3-тиазина |
| EP1022278A4 (en) * | 1997-04-02 | 2000-12-27 | Rimma Iliinichna Ashkinazi | TETRACYCLIC PYRIMIDINE DERIVATIVES |
| WO2002066443A2 (en) * | 2001-02-21 | 2002-08-29 | Ono Pharmaceutical Co., Ltd. | 2-thioxo-1,2,3,4-tetrahydropyrimidine derivatives |
| CN104844628B (zh) * | 2015-04-16 | 2017-01-18 | 石家庄学院 | 2H,6H‑嘧啶并[2,1‑b][1,3]噻嗪类衍生物及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1275804A (en) * | 1969-07-03 | 1972-05-24 | Seperic | Improvements in or relating to new sulphur containing derivatives of pyrimidine, their preparation and their applications |
| US4753946A (en) * | 1987-04-08 | 1988-06-28 | E. R. Squibb & Sons, Inc. | Pyrimidinecarboxylic acid derivatives |
-
1989
- 1989-07-19 HU HU893658A patent/HU203878B/hu not_active IP Right Cessation
-
1990
- 1990-07-12 ZA ZA905456A patent/ZA905456B/xx unknown
- 1990-07-12 BE BE9000710A patent/BE1004489A3/fr not_active IP Right Cessation
- 1990-07-16 IL IL9509190A patent/IL95091A/en not_active IP Right Cessation
- 1990-07-17 PL PL90286086A patent/PL163653B1/pl unknown
- 1990-07-18 YU YU141290A patent/YU47949B/sh unknown
- 1990-07-18 DD DD90342877A patent/DD296930A5/de not_active IP Right Cessation
- 1990-07-18 CZ CS903571A patent/CZ280445B6/cs unknown
- 1990-07-18 JP JP2188163A patent/JPH03148284A/ja active Pending
- 1990-07-18 KR KR1019900010863A patent/KR940006637B1/ko not_active Expired - Fee Related
- 1990-07-19 GB GB9015831A patent/GB2234508B/en not_active Expired - Fee Related
- 1990-07-19 US US07/555,943 patent/US5071849A/en not_active Expired - Fee Related
- 1990-07-19 FR FR9009223A patent/FR2649981B1/fr not_active Expired - Fee Related
- 1990-07-19 CA CA002021556A patent/CA2021556A1/en not_active Abandoned
- 1990-07-19 IT IT02098290A patent/IT1249212B/it active IP Right Grant
- 1990-07-19 ES ES9001960A patent/ES2027492A6/es not_active Expired - Lifetime
- 1990-07-19 RU SU904830599A patent/RU2022965C1/ru active
- 1990-07-19 EP EP19900113841 patent/EP0409223A3/de not_active Ceased
- 1990-07-19 BG BG092478A patent/BG60209B2/bg unknown
- 1990-07-19 AT AT0152890A patent/AT399879B/de not_active IP Right Cessation
-
1991
- 1991-11-15 GR GR91300031T patent/GR910300031T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1249212B (it) | 1995-02-20 |
| YU47949B (sh) | 1996-07-24 |
| GB9015831D0 (en) | 1990-09-05 |
| PL163653B1 (pl) | 1994-04-29 |
| ATA152890A (de) | 1994-12-15 |
| JPH03148284A (ja) | 1991-06-25 |
| EP0409223A2 (de) | 1991-01-23 |
| YU141290A (sh) | 1992-12-21 |
| RU2022965C1 (ru) | 1994-11-15 |
| IT9020982A0 (it) | 1990-07-19 |
| FR2649981B1 (fr) | 1993-07-30 |
| ZA905456B (en) | 1994-08-09 |
| GR910300031T1 (en) | 1991-11-15 |
| PL286086A1 (en) | 1991-07-29 |
| CZ357190A3 (en) | 1995-10-18 |
| BE1004489A3 (fr) | 1992-12-01 |
| BG60209B2 (bg) | 1993-12-30 |
| GB2234508A (en) | 1991-02-06 |
| KR910002875A (ko) | 1991-02-26 |
| KR940006637B1 (ko) | 1994-07-23 |
| HUT54352A (en) | 1991-02-28 |
| GB2234508B (en) | 1993-01-06 |
| ES2027492A6 (es) | 1992-06-01 |
| FR2649981A1 (fr) | 1991-01-25 |
| AT399879B (de) | 1995-08-25 |
| IL95091A (en) | 1994-11-11 |
| EP0409223A3 (en) | 1991-11-21 |
| IL95091A0 (en) | 1991-06-10 |
| IT9020982A1 (it) | 1992-01-19 |
| CZ280445B6 (cs) | 1996-01-17 |
| CA2021556A1 (en) | 1991-01-20 |
| US5071849A (en) | 1991-12-10 |
| HU203878B (en) | 1991-10-28 |
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| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |