HRP20200638T1 - Derivati etinila - Google Patents
Derivati etinila Download PDFInfo
- Publication number
- HRP20200638T1 HRP20200638T1 HRP20200638TT HRP20200638T HRP20200638T1 HR P20200638 T1 HRP20200638 T1 HR P20200638T1 HR P20200638T T HRP20200638T T HR P20200638TT HR P20200638 T HRP20200638 T HR P20200638T HR P20200638 T1 HRP20200638 T1 HR P20200638T1
- Authority
- HR
- Croatia
- Prior art keywords
- heptan
- diazabicyclo
- pyridin
- methyl
- compound
- Prior art date
Links
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- VPJZBZSJQDZUQZ-DLBZAZTESA-N (1R,5S)-2-[5-[2-(2,5-difluorophenyl)ethynyl]pyridin-2-yl]-4-methyl-2,4-diazabicyclo[3.2.0]heptan-3-one Chemical compound FC1=C(C=C(C=C1)F)C#CC=1C=CC(=NC=1)N1[C@@H]2CC[C@@H]2N(C1=O)C VPJZBZSJQDZUQZ-DLBZAZTESA-N 0.000 claims 1
- CALZXDLVWVLRTP-DLBZAZTESA-N (1R,5S)-2-[5-[2-(3-fluorophenyl)ethynyl]pyridin-2-yl]-4-methyl-2,4-diazabicyclo[3.2.0]heptan-3-one Chemical compound FC=1C=C(C=CC=1)C#CC=1C=CC(=NC=1)N1[C@@H]2CC[C@@H]2N(C1=O)C CALZXDLVWVLRTP-DLBZAZTESA-N 0.000 claims 1
- PSBSYTKPYXXIMG-DLBZAZTESA-N (1R,5S)-2-[5-[2-(4-fluorophenyl)ethynyl]pyridin-2-yl]-4-methyl-2,4-diazabicyclo[3.2.0]heptan-3-one Chemical compound FC1=CC=C(C=C1)C#CC=1C=CC(=NC=1)N1[C@@H]2CC[C@@H]2N(C1=O)C PSBSYTKPYXXIMG-DLBZAZTESA-N 0.000 claims 1
- GUFIEMPVYLURJX-SJORKVTESA-N (1R,5S)-2-methyl-4-[5-(2-phenylethynyl)pyridin-2-yl]-2,4-diazabicyclo[3.2.0]heptan-3-one Chemical compound CN1[C@@H]2CC[C@@H]2N(C1=O)C1=NC=C(C=C1)C#CC1=CC=CC=C1 GUFIEMPVYLURJX-SJORKVTESA-N 0.000 claims 1
- VPJZBZSJQDZUQZ-SJORKVTESA-N (1S,5R)-2-[5-[2-(2,5-difluorophenyl)ethynyl]pyridin-2-yl]-4-methyl-2,4-diazabicyclo[3.2.0]heptan-3-one Chemical compound FC1=C(C=C(C=C1)F)C#CC=1C=CC(=NC=1)N1[C@H]2CC[C@H]2N(C1=O)C VPJZBZSJQDZUQZ-SJORKVTESA-N 0.000 claims 1
- CALZXDLVWVLRTP-SJORKVTESA-N (1S,5R)-2-[5-[2-(3-fluorophenyl)ethynyl]pyridin-2-yl]-4-methyl-2,4-diazabicyclo[3.2.0]heptan-3-one Chemical compound FC=1C=C(C=CC=1)C#CC=1C=CC(=NC=1)N1[C@H]2CC[C@H]2N(C1=O)C CALZXDLVWVLRTP-SJORKVTESA-N 0.000 claims 1
- PSBSYTKPYXXIMG-SJORKVTESA-N (1S,5R)-2-[5-[2-(4-fluorophenyl)ethynyl]pyridin-2-yl]-4-methyl-2,4-diazabicyclo[3.2.0]heptan-3-one Chemical compound FC1=CC=C(C=C1)C#CC=1C=CC(=NC=1)N1[C@H]2CC[C@H]2N(C1=O)C PSBSYTKPYXXIMG-SJORKVTESA-N 0.000 claims 1
- GUFIEMPVYLURJX-DLBZAZTESA-N (1S,5R)-2-methyl-4-[5-(2-phenylethynyl)pyridin-2-yl]-2,4-diazabicyclo[3.2.0]heptan-3-one Chemical compound CN1[C@H]2CC[C@H]2N(C1=O)C1=NC=C(C=C1)C#CC1=CC=CC=C1 GUFIEMPVYLURJX-DLBZAZTESA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 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
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4166—1,3-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. phenytoin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/22—Aliphatic unsaturated hydrocarbons containing carbon-to-carbon triple bonds
-
- 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Claims (7)
1. Spoj, naznačen time, da je predstavljen formulom I
[image]
u kojoj
R1 je vodik ili F;
n je 1 ili 2
ili njegova farmaceutski prihvatljiva kiselinska adicijska sol.
2. Spoj formule I prema patentnom zahtjevu 1, naznačen time, da su to sljedeći spojevi:
(1S,5R)-2-metil-4-(5-(feniletinil)piridin-2-il)-2,4-diazabiciklo[3,2.0]heptan-3-on;
(1R,5S)-2-(5-((4-fluorofenil)etinil)piridin-2-il)-4-metil-2,4-diazabiciklo[3.2.0]heptan-3-on;
(1R,5S)-2-(5-((3-fluorofenil)etinil)piridin-2-il)-4-metil-2,4-diazabiciklo[3.2.0]heptan-3-on; ili
(1R,5S)-2-(5-((2,5-difluorofenil)etinil)piridin-2-il)-4-metil-2,4-diazabiciklo[3.2.0]heptan-3-on.
3. Spoj, naznačen time, da je odabran iz skupine koju čine:
(1R,5S)-2-metil-4-(5-(feniletinil)-piridin-2-il)-2,4-diazabiciklo[3,2.0]heptan-3-on;
(1S,5R)-2-(5-((4-fluorofenil)etinil)piridin-2-il)-4-metil-2,4-diazabiciklo[3.2.0]heptan-3-on;
(1S,5R)-2-(5-((3-fluorofenil)etinil)piridin-2-il)-4-metil-2,4-diazabiciklo[3.2.0]heptan-3-on; i
(1S,5R)-2-(5-((2,5-difluorofenil)etinil)piridin-2-il)-4-metil-2,4-diazabiciklo[3.2.0]heptan-3-on.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 ili 2, naznačen time, da se koristi kao terapeutski aktivna tvar.
5. Postupak za proizvodnju spoja formule I prema bilo kojem od patentnih zahtjeva 1 ili 2, naznačen time, da sadrži reakciju spoja formule II
[image]
u kojoj X je atom halogena odabran između broma ili joda,
s pogodnim aril-acetilenom formule III
[image]
za tvorbu spoja formule I
[image]
pri čemu supstituent R1 je vodik ili fluor, u enantiomerno čistom obliku s apsolutnom stereokemijom kako je nacrtana u formuli I, ili pomoću II u racemičnom obliku i nakon toga kiralnom separacijom I, čime se dobije optički čisti enantiomer; i
prema želji, konverzijom dobivenih spojeva u farmaceutski prihvatljive kiselinske adicijske soli.
6. Farmaceutski pripravak, naznačen time, da sadrži spoj prema bilo kojem od patentnih zahtjeva 1 ili 2 i terapeutski inertni nosač.
7. Spoj prema bilo kojem od patentnih zahtjeva 1 ili 2, naznačen time, da se upotrebljava u liječenju anksioznosti i boli, depresije, Parkinsonove bolesti i gastroezofagealne refluksne bolesti (GERD).
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP15170401 | 2015-06-03 | ||
EP16727661.7A EP3303316B1 (en) | 2015-06-03 | 2016-05-31 | Ethynyl derivatives |
PCT/EP2016/062202 WO2016193234A1 (en) | 2015-06-03 | 2016-05-31 | Ethynyl derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20200638T1 true HRP20200638T1 (hr) | 2020-07-10 |
Family
ID=53276789
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20200638TT HRP20200638T1 (hr) | 2015-06-03 | 2020-04-22 | Derivati etinila |
Country Status (31)
Country | Link |
---|---|
US (2) | US11059766B2 (hr) |
EP (1) | EP3303316B1 (hr) |
JP (1) | JP6603334B2 (hr) |
KR (1) | KR102035048B1 (hr) |
CN (1) | CN107849006B (hr) |
AR (1) | AR104842A1 (hr) |
AU (1) | AU2016273751B2 (hr) |
BR (1) | BR112017023894A2 (hr) |
CA (1) | CA2985301A1 (hr) |
CL (1) | CL2017002969A1 (hr) |
CO (1) | CO2017012260A2 (hr) |
CR (1) | CR20170536A (hr) |
DK (1) | DK3303316T3 (hr) |
ES (1) | ES2786673T3 (hr) |
HK (1) | HK1249096A1 (hr) |
HR (1) | HRP20200638T1 (hr) |
HU (1) | HUE048867T2 (hr) |
IL (1) | IL255367B (hr) |
LT (1) | LT3303316T (hr) |
MA (1) | MA42508B1 (hr) |
MX (1) | MX2017015043A (hr) |
PE (1) | PE20180358A1 (hr) |
PH (1) | PH12017502128A1 (hr) |
PL (1) | PL3303316T3 (hr) |
PT (1) | PT3303316T (hr) |
RS (1) | RS60199B1 (hr) |
RU (1) | RU2712633C1 (hr) |
SI (1) | SI3303316T1 (hr) |
TW (1) | TWI589571B (hr) |
UA (1) | UA120309C2 (hr) |
WO (1) | WO2016193234A1 (hr) |
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FI90869C (fi) | 1986-11-14 | 1994-04-11 | Tanabe Seiyaku Co | Menetelmä lääkeaineena käyttökelpoisten imidatsolidinonijohdannaisten valmistamiseksi |
JP3213780B2 (ja) | 1993-12-21 | 2001-10-02 | キヤノン株式会社 | 光学活性化合物、これを含有する液晶組成物、該液晶組成物を用いた液晶素子並びにこれらを用いた表示方法、表示装置 |
GB9510744D0 (en) | 1995-05-26 | 1995-07-19 | Zeneca Ltd | Chemical process |
JPH09151179A (ja) | 1995-11-30 | 1997-06-10 | Canon Inc | 光学活性化合物、これを含む液晶組成物、それを有する液晶素子、それらを用いた液晶装置及び表示方法 |
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AU2000269030A1 (en) | 2000-08-11 | 2002-02-25 | Monsanto Technology Llc | Broad-spectrum delta-endotoxins |
US6410728B1 (en) | 2000-08-31 | 2002-06-25 | Abbott Laboratories | Oxazolidinone chemotherapeutic agents |
GB0103045D0 (en) * | 2001-02-07 | 2001-03-21 | Novartis Ag | Organic Compounds |
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