CS211388B2 - Method of preparation of substituted chinolizidine and indolizidine derivatives - Google Patents
Method of preparation of substituted chinolizidine and indolizidine derivatives Download PDFInfo
- Publication number
- CS211388B2 CS211388B2 CS783027A CS302778A CS211388B2 CS 211388 B2 CS211388 B2 CS 211388B2 CS 783027 A CS783027 A CS 783027A CS 302778 A CS302778 A CS 302778A CS 211388 B2 CS211388 B2 CS 211388B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- preparation
- starting compound
- quaternary
- methanol
- quinolizidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- HAJKHJOABGFIGP-UHFFFAOYSA-N indolizidine Chemical class C1CCCN2CCCC21 HAJKHJOABGFIGP-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- LJPZHJUSICYOIX-UHFFFAOYSA-N quinolizidine Chemical class C1CCCC2CCCCN21 LJPZHJUSICYOIX-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract 3
- 230000018044 dehydration Effects 0.000 claims abstract 2
- 238000006297 dehydration reaction Methods 0.000 claims abstract 2
- 239000007858 starting material Substances 0.000 claims 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 12
- GELITQBPLDAKOJ-UHFFFAOYSA-N 3-benzhydrylidene-2,5,6,7,8,8a-hexahydro-1H-indolizine Chemical group C1(=CC=CC=C1)C(=C1CCC2CCCCN12)C1=CC=CC=C1 GELITQBPLDAKOJ-UHFFFAOYSA-N 0.000 claims 2
- XKIPXPURXMUMAA-UHFFFAOYSA-N 7-(dithiophen-2-ylmethylidene)-1,2,3,4,6,8,9,9a-octahydroquinolizine Chemical compound C1CC2CCCCN2CC1=C(C=1SC=CC=1)C1=CC=CS1 XKIPXPURXMUMAA-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- -1 for example Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- XJWRSCXGDIDATI-UHFFFAOYSA-N 2-(dithiophen-2-ylmethylidene)-3,5,6,7,8,8a-hexahydro-1h-indolizine Chemical group C1C2CCCCN2CC1=C(C=1SC=CC=1)C1=CC=CS1 XJWRSCXGDIDATI-UHFFFAOYSA-N 0.000 claims 1
- FDJHPXXRMFOMJR-UHFFFAOYSA-N 2-benzhydrylidene-3,5,6,7,8,8a-hexahydro-1h-indolizine Chemical compound C1C2CCCCN2CC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 FDJHPXXRMFOMJR-UHFFFAOYSA-N 0.000 claims 1
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 claims 1
- VGRPVFKNUWHHCC-UHFFFAOYSA-N 8-(dithiophen-2-ylmethylidene)-1,2,3,4,6,7,9,9a-octahydroquinolizine Chemical compound C1C2CCCCN2CCC1=C(C=1SC=CC=1)C1=CC=CS1 VGRPVFKNUWHHCC-UHFFFAOYSA-N 0.000 claims 1
- VFXZIMFKMXRVKV-UHFFFAOYSA-N 8-benzhydrylidene-1,2,3,4,6,7,9,9a-octahydroquinolizine Chemical compound C1C2CCCCN2CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 VFXZIMFKMXRVKV-UHFFFAOYSA-N 0.000 claims 1
- JCNVNRJWEIBDRZ-UHFFFAOYSA-N 9-(dithiophen-2-ylmethylidene)-1,2,3,4,6,7,8,9a-octahydroquinolizine Chemical compound C12CCCCN2CCCC1=C(C=1SC=CC=1)C1=CC=CS1 JCNVNRJWEIBDRZ-UHFFFAOYSA-N 0.000 claims 1
- PAQDLFGONOLCCG-UHFFFAOYSA-N 9-benzhydrylidene-1,2,3,4,6,7,8,9a-octahydroquinolizine Chemical group C12CCCCN2CCCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 PAQDLFGONOLCCG-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229940125797 compound 12 Drugs 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims 1
- 229940057952 methanol Drugs 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 1
- 238000005956 quaternization reaction Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 230000001004 anti-acetylcholinic effect Effects 0.000 description 4
- 229930003347 Atropine Natural products 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- 229960000396 atropine Drugs 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- UCGJZJXOPSNTGZ-UHFFFAOYSA-M Prifinium bromide Chemical compound [Br-].CC1[N+](CC)(CC)CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 UCGJZJXOPSNTGZ-UHFFFAOYSA-M 0.000 description 1
- QTSXMEPZSHLZFF-UHFFFAOYSA-M Timepidium bromide Chemical compound [Br-].C1[N+](C)(C)CC(OC)CC1=C(C=1SC=CC=1)C1=CC=CS1 QTSXMEPZSHLZFF-UHFFFAOYSA-M 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 229960005275 prifinium bromide Drugs 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- 229960003737 timepidium bromide Drugs 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/02—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing not further condensed quinolizine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5526677A JPS53141294A (en) | 1977-05-16 | 1977-05-16 | 22diphenylmethylenequinolitidine and process for preparing same |
| JP10727077A JPS5441892A (en) | 1977-09-08 | 1977-09-08 | Quaternary salt derivative |
| JP13352677A JPS5467020A (en) | 1977-11-09 | 1977-11-09 | 33diphenylmethylenquinolysine quarternary salt derivative |
| JP14661377A JPS5481297A (en) | 1977-12-08 | 1977-12-08 | 11diphenylmethylene quinolitidine tertiary salt derivative |
| JP15284177A JPS5488293A (en) | 1977-12-21 | 1977-12-21 | Quaternary salt derivative |
| JP2153478A JPS54115396A (en) | 1978-02-28 | 1978-02-28 | 22dithienylmethylene quinolitidine quaternary salt derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS211388B2 true CS211388B2 (en) | 1982-02-26 |
Family
ID=27548989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS783027A CS211388B2 (en) | 1977-05-16 | 1978-05-11 | Method of preparation of substituted chinolizidine and indolizidine derivatives |
Country Status (24)
| Country | Link |
|---|---|
| AR (1) | AR223814A1 (de) |
| AT (1) | AT364362B (de) |
| BE (1) | BE866988A (de) |
| BG (1) | BG30018A3 (de) |
| CA (1) | CA1100970A (de) |
| CH (1) | CH635341A5 (de) |
| CS (1) | CS211388B2 (de) |
| DD (1) | DD142447A5 (de) |
| DE (1) | DE2820687C2 (de) |
| DK (1) | DK211278A (de) |
| FI (1) | FI64368C (de) |
| FR (1) | FR2390956A1 (de) |
| GB (1) | GB1602927A (de) |
| GR (1) | GR64422B (de) |
| HU (1) | HU181441B (de) |
| IT (1) | IT1113139B (de) |
| NL (1) | NL186006C (de) |
| NO (1) | NO149432C (de) |
| NZ (1) | NZ187258A (de) |
| PL (1) | PL115343B1 (de) |
| PT (1) | PT68009B (de) |
| SE (1) | SE443787B (de) |
| SU (1) | SU953980A3 (de) |
| YU (1) | YU40705B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994013289A1 (en) * | 1992-12-10 | 1994-06-23 | Tsentr Po Khimii Lekarstvennykh Sredstv | Pharmaceutical compound with anti-ulcer properties |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4089961A (en) * | 1976-11-08 | 1978-05-16 | Smithkline Corporation | Antipsychotically useful quinolizidylidene derivatives of xanthenes, thioxanthenes and dibenzoxepins |
-
1978
- 1978-04-24 BG BG039520A patent/BG30018A3/xx unknown
- 1978-05-03 IT IT7822967A patent/IT1113139B/it active
- 1978-05-08 CA CA302,858A patent/CA1100970A/en not_active Expired
- 1978-05-08 PT PT68009A patent/PT68009B/pt unknown
- 1978-05-08 GR GR56170A patent/GR64422B/el unknown
- 1978-05-11 CS CS783027A patent/CS211388B2/cs unknown
- 1978-05-11 AT AT0342378A patent/AT364362B/de not_active IP Right Cessation
- 1978-05-11 DE DE2820687A patent/DE2820687C2/de not_active Expired
- 1978-05-11 FR FR7814002A patent/FR2390956A1/fr active Granted
- 1978-05-12 DD DD78205365A patent/DD142447A5/de unknown
- 1978-05-12 BE BE2056968A patent/BE866988A/xx not_active IP Right Cessation
- 1978-05-12 NO NO781693A patent/NO149432C/no unknown
- 1978-05-12 SE SE7805513A patent/SE443787B/sv not_active IP Right Cessation
- 1978-05-12 DK DK211278A patent/DK211278A/da not_active Application Discontinuation
- 1978-05-12 NZ NZ187258A patent/NZ187258A/xx unknown
- 1978-05-12 SU SU782616071A patent/SU953980A3/ru active
- 1978-05-15 FI FI781525A patent/FI64368C/fi not_active IP Right Cessation
- 1978-05-15 PL PL1978206809A patent/PL115343B1/pl unknown
- 1978-05-16 NL NLAANVRAGE7805272,A patent/NL186006C/xx not_active IP Right Cessation
- 1978-05-16 HU HU78HO2074A patent/HU181441B/hu not_active IP Right Cessation
- 1978-05-16 GB GB17814/78A patent/GB1602927A/en not_active Expired
- 1978-05-16 CH CH528678A patent/CH635341A5/de not_active IP Right Cessation
- 1978-05-16 YU YU1177/78A patent/YU40705B/xx unknown
- 1978-05-16 AR AR272202A patent/AR223814A1/es active
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