FI111943B - Analogiamenetelmä terapeuttisesti käyttökelpoisen enantiomeerisen yhdisteen valmistamiseksi, joka on (S)- tai (R)-2-[3-[4-(3-kloorifenyyli)-1-(2-alkyyli)-piperatsinyyli]propyyli]-1,2,4-triatsolo[4,3-a]pyridin-3-(2H)-oni, ja välituotteet - Google Patents
Analogiamenetelmä terapeuttisesti käyttökelpoisen enantiomeerisen yhdisteen valmistamiseksi, joka on (S)- tai (R)-2-[3-[4-(3-kloorifenyyli)-1-(2-alkyyli)-piperatsinyyli]propyyli]-1,2,4-triatsolo[4,3-a]pyridin-3-(2H)-oni, ja välituotteet Download PDFInfo
- Publication number
- FI111943B FI111943B FI956334A FI956334A FI111943B FI 111943 B FI111943 B FI 111943B FI 956334 A FI956334 A FI 956334A FI 956334 A FI956334 A FI 956334A FI 111943 B FI111943 B FI 111943B
- Authority
- FI
- Finland
- Prior art keywords
- chlorophenyl
- triazolo
- propyl
- pyridin
- piperazinyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims description 29
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 title claims description 14
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000000543 intermediate Substances 0.000 title description 4
- 239000002253 acid Substances 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 8
- -1 alkali metal salt Chemical class 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 235000002906 tartaric acid Nutrition 0.000 claims description 4
- 239000011975 tartaric acid Substances 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000001640 fractional crystallisation Methods 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical group C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 claims 1
- WZWAXUTUJORSLR-LREBCSMRSA-N C(=O)(O)[C@H](O)[C@@H](O)C(=O)O.N=1CC(C=CC1)=O Chemical compound C(=O)(O)[C@H](O)[C@@H](O)C(=O)O.N=1CC(C=CC1)=O WZWAXUTUJORSLR-LREBCSMRSA-N 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 229940125773 compound 10 Drugs 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229960001367 tartaric acid Drugs 0.000 description 4
- 108060003345 Adrenergic Receptor Proteins 0.000 description 3
- 102000017910 Adrenergic receptor Human genes 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229940125890 compound Ia Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000006340 racemization Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 230000000707 stereoselective effect Effects 0.000 description 3
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 102000030619 alpha-1 Adrenergic Receptor Human genes 0.000 description 2
- 108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- NYUHTNMLJUXJOS-LURJTMIESA-N ethyl (2s)-2-hydroxy-2-methylsulfonylpropanoate Chemical compound CCOC(=O)[C@@](C)(O)S(C)(=O)=O NYUHTNMLJUXJOS-LURJTMIESA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- FUASZNDGQOZKFQ-MRVPVSSYSA-N (3r)-1-(3-chlorophenyl)-3-methylpiperazin-2-one Chemical compound O=C1[C@@H](C)NCCN1C1=CC=CC(Cl)=C1 FUASZNDGQOZKFQ-MRVPVSSYSA-N 0.000 description 1
- GRBUTWWFTFQSMF-SECBINFHSA-N (3r)-1-(3-chlorophenyl)-3-methylpiperazine Chemical compound C1CN[C@H](C)CN1C1=CC=CC(Cl)=C1 GRBUTWWFTFQSMF-SECBINFHSA-N 0.000 description 1
- QZRFMFLUEOAKNE-UHFFFAOYSA-N 1-n'-(3-chlorophenyl)ethane-1,1-diamine Chemical compound CC(N)NC1=CC=CC(Cl)=C1 QZRFMFLUEOAKNE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- ARFLASKVLJTEJD-SCSAIBSYSA-N ethyl (2r)-2-bromopropanoate Chemical compound CCOC(=O)[C@@H](C)Br ARFLASKVLJTEJD-SCSAIBSYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002101 lytic effect Effects 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
- 210000000056 organ Anatomy 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 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
- PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 1
- 229960003991 trazodone 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
- A61P23/00—Anaesthetics
-
- 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
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT93MI001418A IT1268414B1 (it) | 1993-07-01 | 1993-07-01 | Enantiomeri farmacologicamente attivi |
| ITMI931418 | 1993-07-01 | ||
| PCT/EP1994/002061 WO1995001354A1 (en) | 1993-07-01 | 1994-06-21 | Pharmacologically active enantiomers |
| EP9402061 | 1994-06-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI956334A0 FI956334A0 (fi) | 1995-12-29 |
| FI956334L FI956334L (fi) | 1996-02-19 |
| FI111943B true FI111943B (fi) | 2003-10-15 |
Family
ID=11366510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI956334A FI111943B (fi) | 1993-07-01 | 1995-12-29 | Analogiamenetelmä terapeuttisesti käyttökelpoisen enantiomeerisen yhdisteen valmistamiseksi, joka on (S)- tai (R)-2-[3-[4-(3-kloorifenyyli)-1-(2-alkyyli)-piperatsinyyli]propyyli]-1,2,4-triatsolo[4,3-a]pyridin-3-(2H)-oni, ja välituotteet |
Country Status (29)
| Country | Link |
|---|---|
| US (3) | US5741907A (cs) |
| EP (1) | EP0707587B1 (cs) |
| JP (1) | JP3096065B2 (cs) |
| KR (1) | KR100306018B1 (cs) |
| CN (3) | CN1046281C (cs) |
| AT (1) | ATE158796T1 (cs) |
| AU (1) | AU689478B2 (cs) |
| BG (1) | BG61815B1 (cs) |
| BR (1) | BR9406996A (cs) |
| CA (1) | CA2166470C (cs) |
| CZ (1) | CZ289526B6 (cs) |
| DE (1) | DE69405999T2 (cs) |
| DK (1) | DK0707587T3 (cs) |
| ES (1) | ES2111309T3 (cs) |
| FI (1) | FI111943B (cs) |
| GE (1) | GEP19991791B (cs) |
| GR (1) | GR3025806T3 (cs) |
| HU (1) | HU221631B1 (cs) |
| IT (1) | IT1268414B1 (cs) |
| LV (1) | LV11546B (cs) |
| NO (1) | NO305957B1 (cs) |
| NZ (1) | NZ268014A (cs) |
| PL (1) | PL181831B1 (cs) |
| RO (2) | RO121031B1 (cs) |
| RU (1) | RU2128180C1 (cs) |
| SK (1) | SK281060B6 (cs) |
| UA (1) | UA53607C2 (cs) |
| WO (1) | WO1995001354A1 (cs) |
| ZA (1) | ZA944570B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1268414B1 (it) * | 1993-07-01 | 1997-02-27 | Angelini Francesco Ist Ricerca | Enantiomeri farmacologicamente attivi |
| JP2009018992A (ja) * | 2007-07-10 | 2009-01-29 | Sumitomo Chemical Co Ltd | 光学活性ミルタザピンの製造方法 |
| RU2706700C1 (ru) | 2019-09-24 | 2019-11-20 | Общество с ограниченной ответственностью "Научно-производственная компания "СКиФФ" | Фармацевтическая композиция для коррекции поведения кошек и собак в стрессовых ситуациях |
| US20230391771A1 (en) * | 2020-10-07 | 2023-12-07 | Amgen Inc. | Process for racemizing and isolating atropisomers of 7-chloro-6-fluoro-1-(2-isopropyl-4-methylpyridin-3-yl)pyrido[2,3-d]pyrimidine-2,4(1h,3h)-dione |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3365453A (en) * | 1963-10-28 | 1968-01-23 | Sterling Drug Inc | 1-phenyl-4-lower-alkyl-2-piperazinones |
| IT1066857B (it) * | 1965-12-15 | 1985-03-12 | Acraf | Derivati della s ipiazolo 4.3 a piridina e processi per la loro preparazione |
| SU368258A1 (ru) * | 1970-01-27 | 1973-01-26 | Днепчопетровский химико технологический институт Ф. Э. Дзержинского | Способ получения 1,4-диарил-2-карбоксиметил- 3-оксопиперазинов |
| US5303837A (en) * | 1991-03-05 | 1994-04-19 | Portola Packaging, Inc. | One-piece fitment and plug with tamper-evident band |
| US5739334A (en) * | 1992-01-17 | 1998-04-14 | Istituto Ricerca Francesco Angelini S.P.A. | Alkyl derivatives of trazodone with CNS activity |
| GEP20001939B (en) | 1992-01-17 | 2000-02-05 | Angelini Ricerca S P A Soc Consortile | Alkyl Derivatives of Trazodone with CNS Activity |
| IT1268414B1 (it) * | 1993-07-01 | 1997-02-27 | Angelini Francesco Ist Ricerca | Enantiomeri farmacologicamente attivi |
| US5399765A (en) * | 1994-05-23 | 1995-03-21 | Sepracor, Inc. | Enantioselective preparation of optically pure albuterol |
-
1993
- 1993-07-01 IT IT93MI001418A patent/IT1268414B1/it active IP Right Grant
-
1994
- 1994-06-21 CZ CZ19953485A patent/CZ289526B6/cs not_active IP Right Cessation
- 1994-06-21 AT AT94919660T patent/ATE158796T1/de not_active IP Right Cessation
- 1994-06-21 US US08/564,276 patent/US5741907A/en not_active Expired - Fee Related
- 1994-06-21 RO ROA200100015A patent/RO121031B1/ro unknown
- 1994-06-21 DK DK94919660.4T patent/DK0707587T3/da active
- 1994-06-21 KR KR1019950705994A patent/KR100306018B1/ko not_active Expired - Fee Related
- 1994-06-21 SK SK1664-95A patent/SK281060B6/sk not_active IP Right Cessation
- 1994-06-21 ES ES94919660T patent/ES2111309T3/es not_active Expired - Lifetime
- 1994-06-21 DE DE69405999T patent/DE69405999T2/de not_active Expired - Fee Related
- 1994-06-21 EP EP94919660A patent/EP0707587B1/en not_active Expired - Lifetime
- 1994-06-21 NZ NZ268014A patent/NZ268014A/xx not_active IP Right Cessation
- 1994-06-21 BR BR9406996A patent/BR9406996A/pt not_active Application Discontinuation
- 1994-06-21 CA CA002166470A patent/CA2166470C/en not_active Expired - Fee Related
- 1994-06-21 RU RU96104371A patent/RU2128180C1/ru not_active IP Right Cessation
- 1994-06-21 WO PCT/EP1994/002061 patent/WO1995001354A1/en active IP Right Grant
- 1994-06-21 CN CN94193226A patent/CN1046281C/zh not_active Expired - Fee Related
- 1994-06-21 HU HU9503876A patent/HU221631B1/hu not_active IP Right Cessation
- 1994-06-21 PL PL94312419A patent/PL181831B1/pl not_active IP Right Cessation
- 1994-06-21 RO RO95-02315A patent/RO116899B1/ro unknown
- 1994-06-21 UA UA96010331A patent/UA53607C2/uk unknown
- 1994-06-21 JP JP07503250A patent/JP3096065B2/ja not_active Expired - Fee Related
- 1994-06-21 GE GEAP19943025A patent/GEP19991791B/en unknown
- 1994-06-21 AU AU70729/94A patent/AU689478B2/en not_active Ceased
- 1994-06-24 ZA ZA944570A patent/ZA944570B/xx unknown
-
1995
- 1995-12-29 FI FI956334A patent/FI111943B/fi active
- 1995-12-29 NO NO955345A patent/NO305957B1/no unknown
-
1996
- 1996-01-26 LV LVP-96-17A patent/LV11546B/en unknown
- 1996-02-01 BG BG100331A patent/BG61815B1/bg unknown
-
1997
- 1997-12-22 US US08/995,988 patent/US5817815A/en not_active Expired - Fee Related
- 1997-12-30 GR GR970403452T patent/GR3025806T3/el unknown
-
1998
- 1998-05-13 US US09/076,845 patent/US5973150A/en not_active Expired - Fee Related
- 1998-07-29 CN CNB98116661XA patent/CN1136201C/zh not_active Expired - Fee Related
- 1998-07-29 CN CNB981166601A patent/CN1136200C/zh not_active Expired - Fee Related
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