CS228116B2 - Production of 3-nitro-4,5-dihydropyrrole-1,4,5,6-tetrahydropyridine and -1,2,3,6-tetrahydropyrimidine derivatives - Google Patents
Production of 3-nitro-4,5-dihydropyrrole-1,4,5,6-tetrahydropyridine and -1,2,3,6-tetrahydropyrimidine derivatives Download PDFInfo
- Publication number
- CS228116B2 CS228116B2 CS793724A CS372479A CS228116B2 CS 228116 B2 CS228116 B2 CS 228116B2 CS 793724 A CS793724 A CS 793724A CS 372479 A CS372479 A CS 372479A CS 228116 B2 CS228116 B2 CS 228116B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- nitro
- formula
- substituted
- histamine
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- 229940058307 antinematodal tetrahydropyrimidine derivative Drugs 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- HDDZCXUNYDOURD-UHFFFAOYSA-N N1C=CCCC1.[N+](=O)([O-])C1=CNCC1 Chemical compound N1C=CCCC1.[N+](=O)([O-])C1=CNCC1 HDDZCXUNYDOURD-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- -1 2-substituted-2-aza-1,3-propanediyl group Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 6
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 5
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- 229910052736 halogen Inorganic materials 0.000 claims description 4
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 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
- 125000005496 phosphonium group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
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- OXOKINGYIGMVHW-UHFFFAOYSA-N 4-nitro-2,3-dihydro-1h-pyrrole Chemical compound [O-][N+](=O)C1=CNCC1 OXOKINGYIGMVHW-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims 1
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- 150000003254 radicals Chemical class 0.000 claims 1
- 150000005326 tetrahydropyrimidines Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 12
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- 229920001277 pectin Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 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
- 239000003826 tablet Substances 0.000 description 1
- 230000006794 tachycardia Effects 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 230000000304 vasodilatating effect Effects 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
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/12—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
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)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2411678 | 1978-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS228116B2 true CS228116B2 (en) | 1984-05-14 |
Family
ID=10206649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS793724A CS228116B2 (en) | 1978-05-30 | 1979-05-30 | Production of 3-nitro-4,5-dihydropyrrole-1,4,5,6-tetrahydropyridine and -1,2,3,6-tetrahydropyrimidine derivatives |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US4238493A (de) |
| EP (1) | EP0005984B1 (de) |
| JP (1) | JPS54157584A (de) |
| AR (1) | AR222999A1 (de) |
| AT (1) | AT375367B (de) |
| AU (1) | AU522259B2 (de) |
| BG (1) | BG31649A3 (de) |
| CA (1) | CA1118774A (de) |
| CS (1) | CS228116B2 (de) |
| DD (1) | DD144057A5 (de) |
| DE (1) | DE2965716D1 (de) |
| DK (1) | DK223979A (de) |
| ES (1) | ES481076A1 (de) |
| FI (1) | FI791737A7 (de) |
| GR (1) | GR68500B (de) |
| HU (1) | HU181960B (de) |
| IE (1) | IE48510B1 (de) |
| IL (1) | IL57416A (de) |
| NO (1) | NO151322C (de) |
| PL (1) | PL117921B1 (de) |
| PT (1) | PT69686A (de) |
| RO (1) | RO78154A (de) |
| SU (1) | SU888815A3 (de) |
| YU (1) | YU127179A (de) |
| ZA (1) | ZA792608B (de) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL57416A (en) * | 1978-05-30 | 1983-03-31 | Smith Kline French Lab | Nitro compounds,processes for preparing them and compositions containing them |
| US4405624A (en) * | 1978-05-30 | 1983-09-20 | Smith Kline & French Laboratories Limited | Nitro-substituted dihydropyrroles and tetrahydropyridines, compositions, compounds, and medicinal use |
| IL61234A (en) * | 1979-10-24 | 1984-03-30 | Smith Kline French Lab | Guanidino thiazolyl alkylamino(alkylthioalkylamino)nitrotetrahydropyridines,process for preparing them and pharmaceutical compositions containing them |
| PT72320B (en) * | 1980-01-08 | 1982-07-23 | Glaxo Group Ltd | Process for preparation of a furan derivative |
| US4350696A (en) * | 1980-03-08 | 1982-09-21 | Pfizer Inc. | Imidazole derivatives, process for their preparation and pharmaceutical compositions thereof |
| ZW21281A1 (en) * | 1980-10-01 | 1981-11-18 | Smith Kline French Lab | Amine derivatives |
| US4439437A (en) * | 1981-04-28 | 1984-03-27 | Smith Kline & French Laboratories Limited | 2-[2-Thiazolyl or 2-guanidino-4-thiazolyl methylthioethyl(or butyl)amino]-3-(hydroxy or carboxy)pyridines, compositions containing same and method of use |
| IE53068B1 (en) * | 1981-06-15 | 1988-05-25 | Merck & Co Inc | Diamino isothiazole-1-oxides and -1,1-dioxides as gastic secretion inhibitors |
| PT75074B (en) * | 1981-06-27 | 1986-02-26 | Smith Kline French Lab | Process for preparing certain pyrimidone derivatives and compositions containing them |
| US4525477A (en) * | 1981-12-02 | 1985-06-25 | Smith Kline & French Laboratories Limited | 2-Thiazolyl, isothiazolyl, oxazolyl and isoxazolyl alkylamino-3-nitro-heterocyclic compounds |
| AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
| GR82004B (de) * | 1983-06-30 | 1984-12-12 | American Home Prod | |
| IN170284B (de) * | 1988-10-26 | 1992-03-07 | Takeda Chemical Industries Ltd | |
| EP0375613A3 (de) * | 1988-12-21 | 1990-11-28 | Ciba-Geigy Ag | Nitroenamine |
| US6133291A (en) * | 1998-10-16 | 2000-10-17 | Schering Corporation | N-(imidazolylalkyl)substituted cyclic amines as histamine-H3 agonists or antagonists |
| US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980781A (en) * | 1966-03-31 | 1976-09-14 | Imperial Chemical Industries Limited | Fungicidal composition and method containing 2-amino-pyrimidines |
| GB1223686A (en) | 1967-02-24 | 1971-03-03 | Ici Ltd | Salts of pyrimidine derivatives and the use thereof as fungicides |
| DE1617705C3 (de) * | 1966-12-19 | 1973-10-11 | Oreal | Kosmetisches Mittel fur die Haar behandlung |
| US3518251A (en) * | 1967-06-07 | 1970-06-30 | Geigy Ag J R | Certain aminoalkylamino substituted azacycloalkenes |
| US3968216A (en) * | 1969-10-29 | 1976-07-06 | Smith Kline & French Laboratories Limited | Method of inhibiting histamine activity with guanidine compounds |
| BE758146A (fr) * | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Derives de l'amidine |
| US3950353A (en) * | 1971-03-09 | 1976-04-13 | Smith Kline & French Laboratories Limited | Pharmacologically active thiourea and urea compounds |
| US3905984A (en) * | 1971-03-09 | 1975-09-16 | Smith Kline French Lab | Pyridyl substituted thioalkyl-and oxyalkyl-thioureas and ureas |
| US3920822A (en) * | 1972-09-05 | 1975-11-18 | Smith Kline French Lab | Inhibition of histamine activity with cyanoguanidines |
| GB1419994A (en) * | 1973-05-03 | 1976-01-07 | Smith Kline French Lab | Heterocyclicalkylaminotheterocyclic compounds methods for their preparation and compositions comprising them |
| GB1421792A (en) * | 1973-05-17 | 1976-01-21 | Smith Kline French Lab | Heterocyclic substituted-1, 1-diamino-ethylene derivatives methods for their preparation and compositions containing them |
| US4005205A (en) * | 1974-04-24 | 1977-01-25 | Smith Kline & French Laboratories Limited | Compositions and methods for inhibiting H2 histamine receptors |
| CH595061A5 (de) * | 1974-05-10 | 1978-01-31 | Ciba Geigy Ag | |
| US4166856A (en) * | 1975-05-21 | 1979-09-04 | Smith Kline & French Laboratories Limited | Thiazole and isothiazole derivative as blockers of histamine H2 -receptors |
| GB1563090A (en) * | 1975-07-31 | 1980-03-19 | Smith Kline French Lab | Cyclobutene-diones |
| IN146736B (de) * | 1975-10-02 | 1979-08-25 | Smith Kline French Lab | |
| US4154834A (en) * | 1975-12-29 | 1979-05-15 | Smith Kline & French Laboratories Limited | Substituted isocytosines having histamine H2 -antagonist activity |
| GB1565966A (en) * | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
| DE2752820A1 (de) * | 1977-11-26 | 1979-05-31 | Bayer Ag | Neue nitrosubstituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4297498A (en) * | 1978-01-30 | 1981-10-27 | Mead Johnson & Company | 4-Tertiary-amino-2,6-diaminopyridine 1-oxides |
| IL57416A (en) * | 1978-05-30 | 1983-03-31 | Smith Kline French Lab | Nitro compounds,processes for preparing them and compositions containing them |
-
1979
- 1979-05-28 IL IL57416A patent/IL57416A/xx unknown
- 1979-05-28 ZA ZA792608A patent/ZA792608B/xx unknown
- 1979-05-29 SU SU792772964A patent/SU888815A3/ru active
- 1979-05-29 DE DE7979300972T patent/DE2965716D1/de not_active Expired
- 1979-05-29 NO NO791763A patent/NO151322C/no unknown
- 1979-05-29 EP EP79300972A patent/EP0005984B1/de not_active Expired
- 1979-05-29 JP JP6739979A patent/JPS54157584A/ja active Pending
- 1979-05-29 HU HU79SI1694A patent/HU181960B/hu unknown
- 1979-05-29 PT PT69686A patent/PT69686A/pt unknown
- 1979-05-29 CA CA000328543A patent/CA1118774A/en not_active Expired
- 1979-05-30 AR AR276722A patent/AR222999A1/es active
- 1979-05-30 ES ES481076A patent/ES481076A1/es not_active Expired
- 1979-05-30 US US06/043,785 patent/US4238493A/en not_active Expired - Lifetime
- 1979-05-30 GR GR59217A patent/GR68500B/el unknown
- 1979-05-30 FI FI791737A patent/FI791737A7/fi not_active Application Discontinuation
- 1979-05-30 CS CS793724A patent/CS228116B2/cs unknown
- 1979-05-30 BG BG043782A patent/BG31649A3/xx unknown
- 1979-05-30 DD DD79213272A patent/DD144057A5/de unknown
- 1979-05-30 AT AT0395179A patent/AT375367B/de not_active IP Right Cessation
- 1979-05-30 AU AU47580/79A patent/AU522259B2/en not_active Ceased
- 1979-05-30 YU YU01271/79A patent/YU127179A/xx unknown
- 1979-05-30 RO RO7997682A patent/RO78154A/ro unknown
- 1979-05-30 PL PL1979215970A patent/PL117921B1/pl unknown
- 1979-05-30 DK DK223979A patent/DK223979A/da unknown
- 1979-08-08 IE IE1099/79A patent/IE48510B1/en unknown
-
1985
- 1985-03-21 US US06/714,335 patent/US4656176A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO151322C (no) | 1985-03-20 |
| EP0005984A1 (de) | 1979-12-12 |
| ZA792608B (en) | 1980-06-25 |
| FI791737A7 (fi) | 1981-01-01 |
| ATA395179A (de) | 1983-12-15 |
| PL215970A1 (de) | 1980-02-11 |
| BG31649A3 (bg) | 1982-02-15 |
| IL57416A0 (en) | 1979-09-30 |
| RO78154A (ro) | 1982-02-01 |
| US4238493A (en) | 1980-12-09 |
| ES481076A1 (es) | 1980-02-01 |
| IE791099L (en) | 1979-11-30 |
| DK223979A (da) | 1979-12-01 |
| NO791763L (no) | 1979-12-03 |
| CA1118774A (en) | 1982-02-23 |
| PT69686A (en) | 1979-06-01 |
| SU888815A3 (ru) | 1981-12-07 |
| JPS54157584A (en) | 1979-12-12 |
| GR68500B (de) | 1982-01-07 |
| NO151322B (no) | 1984-12-10 |
| AT375367B (de) | 1984-07-25 |
| US4656176A (en) | 1987-04-07 |
| EP0005984B1 (de) | 1983-06-22 |
| DE2965716D1 (en) | 1983-07-28 |
| DD144057A5 (de) | 1980-09-24 |
| HU181960B (en) | 1983-11-28 |
| IL57416A (en) | 1983-03-31 |
| IE48510B1 (en) | 1985-02-20 |
| AR222999A1 (es) | 1981-07-15 |
| AU4758079A (en) | 1979-12-06 |
| YU127179A (en) | 1983-01-21 |
| PL117921B1 (en) | 1981-09-30 |
| AU522259B2 (en) | 1982-05-27 |
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