DD149217A5 - Verfahren zur herstellung von pyrimidonderivaten - Google Patents
Verfahren zur herstellung von pyrimidonderivaten Download PDFInfo
- Publication number
- DD149217A5 DD149217A5 DD80219202A DD21920280A DD149217A5 DD 149217 A5 DD149217 A5 DD 149217A5 DD 80219202 A DD80219202 A DD 80219202A DD 21920280 A DD21920280 A DD 21920280A DD 149217 A5 DD149217 A5 DD 149217A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- radical
- general formula
- group
- pyridyl
- pyrimidone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 230000008569 process Effects 0.000 title claims abstract description 10
- 150000008318 pyrimidones Chemical class 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- -1 2,3-dihydro- 1,4-benzodioxinyl Chemical group 0.000 claims description 78
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 12
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- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 9
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- 125000000217 alkyl group Chemical group 0.000 claims description 7
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- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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- 239000013543 active substance Substances 0.000 description 1
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- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
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- 125000004423 acyloxy group Chemical group 0.000 description 1
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- 239000008272 agar Substances 0.000 description 1
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- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
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- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
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- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 1
- 229960001380 cimetidine Drugs 0.000 description 1
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- 239000008120 corn starch Substances 0.000 description 1
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- 235000019441 ethanol Nutrition 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- IIOWETJNAPDAGC-UHFFFAOYSA-N ethyl 2-formyl-3-(6-methylpyridin-3-yl)propanoate Chemical compound CCOC(=O)C(C=O)CC1=CC=C(C)N=C1 IIOWETJNAPDAGC-UHFFFAOYSA-N 0.000 description 1
- UPQKGGCHMZDTBL-UHFFFAOYSA-N ethyl 3-(6-methylpyridin-3-yl)prop-2-enoate Chemical compound CCOC(=O)C=CC1=CC=C(C)N=C1 UPQKGGCHMZDTBL-UHFFFAOYSA-N 0.000 description 1
- ZABMIGDVOIATQB-UHFFFAOYSA-N ethyl 3-(6-methylpyridin-3-yl)propanoate Chemical compound CCOC(=O)CCC1=CC=C(C)N=C1 ZABMIGDVOIATQB-UHFFFAOYSA-N 0.000 description 1
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- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 239000000938 histamine H1 antagonist Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
- 229960000582 mepyramine Drugs 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 201000003152 motion sickness Diseases 0.000 description 1
- UEYJDXWECYSBCN-UHFFFAOYSA-N n-[5-(furan-2-ylmethyl)-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound O=C1NC(N[N+](=O)[O-])=NC=C1CC1=CC=CO1 UEYJDXWECYSBCN-UHFFFAOYSA-N 0.000 description 1
- QGWDKSNKGFBHBZ-UHFFFAOYSA-N n-[5-(naphthalen-1-ylmethyl)-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound O=C1NC(N[N+](=O)[O-])=NC=C1CC1=CC=CC2=CC=CC=C12 QGWDKSNKGFBHBZ-UHFFFAOYSA-N 0.000 description 1
- DYSDJZQYNYDJBU-UHFFFAOYSA-N n-[5-[(2-methoxypyridin-4-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound C1=NC(OC)=CC(CC=2C(NC(N[N+]([O-])=O)=NC=2)=O)=C1 DYSDJZQYNYDJBU-UHFFFAOYSA-N 0.000 description 1
- PKQFGDMUBKODDI-UHFFFAOYSA-N n-[5-[(3-methoxyphenyl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound COC1=CC=CC(CC=2C(NC(N[N+]([O-])=O)=NC=2)=O)=C1 PKQFGDMUBKODDI-UHFFFAOYSA-N 0.000 description 1
- CCOVEZVZSDAGQQ-UHFFFAOYSA-N n-[5-[(4-methoxypyridin-2-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound COC1=CC=NC(CC=2C(NC(N[N+]([O-])=O)=NC=2)=O)=C1 CCOVEZVZSDAGQQ-UHFFFAOYSA-N 0.000 description 1
- WCCXSTMOFAXKAF-UHFFFAOYSA-N n-[5-[(5,6-dimethylpyridin-3-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound N1=C(C)C(C)=CC(CC=2C(NC(N[N+]([O-])=O)=NC=2)=O)=C1 WCCXSTMOFAXKAF-UHFFFAOYSA-N 0.000 description 1
- RHOIVJHCCZBVSO-UHFFFAOYSA-N n-[5-[(6-methoxypyridin-3-yl)methyl]-6-oxo-1h-pyrimidin-2-yl]nitramide Chemical compound C1=NC(OC)=CC=C1CC1=CN=C(N[N+]([O-])=O)NC1=O RHOIVJHCCZBVSO-UHFFFAOYSA-N 0.000 description 1
- JBBMUXNATHOAFT-UHFFFAOYSA-N n-[6-oxo-5-[(3,4,5-trimethoxyphenyl)methyl]-1h-pyrimidin-2-yl]nitramide Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(NC(N[N+]([O-])=O)=NC=2)=O)=C1 JBBMUXNATHOAFT-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002547 new drug Substances 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
- 239000002674 ointment Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
- 229960000444 pentagastrin Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7906070 | 1979-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD149217A5 true DD149217A5 (de) | 1981-07-01 |
Family
ID=10503327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80219202A DD149217A5 (de) | 1979-02-21 | 1980-02-21 | Verfahren zur herstellung von pyrimidonderivaten |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4521418A (es) |
| EP (1) | EP0015138B1 (es) |
| JP (1) | JPS55115883A (es) |
| AR (1) | AR224392A1 (es) |
| AT (1) | AT377260B (es) |
| AU (1) | AU536194B2 (es) |
| DD (1) | DD149217A5 (es) |
| DE (1) | DE3062310D1 (es) |
| DK (1) | DK74680A (es) |
| ES (1) | ES488772A0 (es) |
| FI (1) | FI800515A7 (es) |
| GR (1) | GR74009B (es) |
| IE (1) | IE49270B1 (es) |
| NO (1) | NO800463L (es) |
| PL (1) | PL222115A1 (es) |
| PT (1) | PT70850A (es) |
| RO (1) | RO79711A (es) |
| ZA (1) | ZA801002B (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4383343A (en) * | 1979-08-09 | 1983-05-17 | Kulka Thomas S | Foot supporting strap for hospital bed |
| US4227271A (en) * | 1979-08-09 | 1980-10-14 | Kulka Thomas S | Foot supporting strap for hospital bed |
| CA1206151A (en) * | 1981-12-28 | 1986-06-17 | Richard P. Pioch | Pyrimidone anti-ulcer agents |
| CA1211111A (en) * | 1982-02-15 | 1986-09-09 | Isao Yanagisawa | Process for preparing novel pyrimidone compounds |
| US4808589A (en) * | 1982-02-20 | 1989-02-28 | Smith Kline & French Laboratories Limited | Pyrimidone derivatives |
| US4444381A (en) * | 1982-05-11 | 1984-04-24 | Wayne Sherwyn J | Operating table accessory, particularly for lumbar laminectomies |
| DE3220118A1 (de) * | 1982-05-28 | 1983-12-01 | Bayer Ag, 5090 Leverkusen | Alkylenverbrueckte guanidinothiazolderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE3306102C1 (de) * | 1983-02-22 | 1984-08-02 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Pyridin-Pyrimidinon-Derivate,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| GB8320505D0 (en) * | 1983-07-29 | 1983-09-01 | Smith Kline French Lab | Chemical compounds |
| US4772704A (en) * | 1983-09-21 | 1988-09-20 | Bristol-Myers Company | 2,5-disubstituted-4(3H)-pyrimidones having histamine H2 -receptor antagonist activity |
| GB8421427D0 (en) * | 1984-08-23 | 1984-09-26 | Smith Kline French Lab | Chemical compounds |
| IT1178026B (it) * | 1984-10-05 | 1987-09-03 | Medosan Ind Biochimi | Derivati del 2-amino-tiazolo |
| JO1410B1 (en) * | 1984-11-03 | 1986-11-30 | سميث كلاين اند فرينش لابوراتوريز ليمتد | Compounds |
| JP2807577B2 (ja) * | 1990-06-15 | 1998-10-08 | エーザイ株式会社 | 環状アミド誘導体 |
| US5611097A (en) * | 1995-08-17 | 1997-03-18 | Dumke; Dan | Foot stop for beds |
| EP4196793A1 (en) | 2020-08-11 | 2023-06-21 | Université de Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1223686A (en) * | 1967-02-24 | 1971-03-03 | Ici Ltd | Salts of pyrimidine derivatives and the use thereof as fungicides |
| US3980781A (en) * | 1966-03-31 | 1976-09-14 | Imperial Chemical Industries Limited | Fungicidal composition and method containing 2-amino-pyrimidines |
| GB1419994A (en) * | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
| IN146736B (es) * | 1975-10-02 | 1979-08-25 | Smith Kline French Lab | |
| US4145546A (en) * | 1975-10-02 | 1979-03-20 | Smith Kline & French Laboratories Limited | 4-Pyrimidone compounds |
| US4216318A (en) * | 1975-12-29 | 1980-08-05 | Smith Kline & French Laboratories Limited | Heterocyclic alkyl 4-pyrimidones |
| MW5076A1 (en) * | 1975-12-29 | 1978-02-08 | Smith Kline French Lab | Pharmacologicalle active compounds |
| US4154834A (en) * | 1975-12-29 | 1979-05-15 | Smith Kline & French Laboratories Limited | Substituted isocytosines having histamine H2 -antagonist activity |
| ZA782129B (en) * | 1977-04-20 | 1979-03-28 | Ici Ltd | Hertocyclic derivatives |
| DE2817078C2 (de) * | 1977-04-20 | 1995-06-14 | Zeneca Ltd | Guanidinderivate |
| US4165378A (en) * | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| US4315009A (en) * | 1978-01-18 | 1982-02-09 | Imperial Chemical Industries Limited | Antisecretory guanidine derivatives and pharmaceutical compositions containing them |
| US4374836A (en) * | 1978-10-16 | 1983-02-22 | Imperial Chemical Industries Ltd. | Antisecretory heterocyclic derivatives, process for their manufacture and pharmaceutical compositions containing them |
-
1980
- 1980-02-12 US US06/120,807 patent/US4521418A/en not_active Expired - Lifetime
- 1980-02-19 GR GR61235A patent/GR74009B/el unknown
- 1980-02-20 IE IE337/80A patent/IE49270B1/en unknown
- 1980-02-20 PT PT70850A patent/PT70850A/pt unknown
- 1980-02-20 JP JP2106580A patent/JPS55115883A/ja active Pending
- 1980-02-20 PL PL22211580A patent/PL222115A1/xx unknown
- 1980-02-20 NO NO800463A patent/NO800463L/no unknown
- 1980-02-20 ES ES488772A patent/ES488772A0/es active Granted
- 1980-02-20 DE DE8080300478T patent/DE3062310D1/de not_active Expired
- 1980-02-20 EP EP80300478A patent/EP0015138B1/en not_active Expired
- 1980-02-21 ZA ZA00801002A patent/ZA801002B/xx unknown
- 1980-02-21 FI FI800515A patent/FI800515A7/fi not_active Application Discontinuation
- 1980-02-21 DK DK74680A patent/DK74680A/da not_active Application Discontinuation
- 1980-02-21 RO RO80100261A patent/RO79711A/ro unknown
- 1980-02-21 AU AU55791/80A patent/AU536194B2/en not_active Ceased
- 1980-02-21 AR AR280058A patent/AR224392A1/es active
- 1980-02-21 DD DD80219202A patent/DD149217A5/de unknown
- 1980-02-21 AT AT0098280A patent/AT377260B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0015138A1 (en) | 1980-09-03 |
| ZA801002B (en) | 1981-03-25 |
| PL222115A1 (es) | 1980-12-01 |
| FI800515A7 (fi) | 1981-01-01 |
| IE800337L (en) | 1980-08-21 |
| AT377260B (de) | 1985-02-25 |
| DE3062310D1 (en) | 1983-04-21 |
| AR224392A1 (es) | 1981-11-30 |
| GR74009B (es) | 1984-06-06 |
| JPS55115883A (en) | 1980-09-06 |
| AU5579180A (en) | 1980-08-28 |
| ATA98280A (de) | 1984-07-15 |
| AU536194B2 (en) | 1984-04-19 |
| EP0015138B1 (en) | 1983-03-16 |
| ES8103078A1 (es) | 1981-02-16 |
| PT70850A (en) | 1980-03-01 |
| DK74680A (da) | 1980-08-22 |
| RO79711A (ro) | 1982-08-17 |
| US4521418A (en) | 1985-06-04 |
| IE49270B1 (en) | 1985-09-04 |
| NO800463L (no) | 1980-08-22 |
| ES488772A0 (es) | 1981-02-16 |
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