NO833147L - Polymorfe forbindelsr, samt fremgangsmaate for fremstilling av slike. - Google Patents
Polymorfe forbindelsr, samt fremgangsmaate for fremstilling av slike.Info
- Publication number
- NO833147L NO833147L NO833147A NO833147A NO833147L NO 833147 L NO833147 L NO 833147L NO 833147 A NO833147 A NO 833147A NO 833147 A NO833147 A NO 833147A NO 833147 L NO833147 L NO 833147L
- Authority
- NO
- Norway
- Prior art keywords
- polymorph
- ici
- solution
- starting material
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- ALCSGJCIESECFD-UHFFFAOYSA-N 5-[3-[[amino(2,2,2-trifluoroethylimino)methyl]amino]-1-pyrazolyl]pentanamide Chemical compound NC(=O)CCCCN1C=CC(NC(N)=NCC(F)(F)F)=N1 ALCSGJCIESECFD-UHFFFAOYSA-N 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 14
- 238000005102 attenuated total reflection Methods 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 9
- 238000002329 infrared spectrum Methods 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 238000010899 nucleation Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229950001902 dimevamide Drugs 0.000 abstract description 2
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- ZUXOHKDGFDBNNW-UHFFFAOYSA-N 5-(3-nitropyrazol-1-yl)pentanenitrile Chemical compound [O-][N+](=O)C=1C=CN(CCCCC#N)N=1 ZUXOHKDGFDBNNW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- MOEIRUOTENBARR-UHFFFAOYSA-N 1-[1-(4-cyanobutyl)pyrazol-3-yl]-2-(2,2,2-trifluoroethyl)guanidine Chemical compound FC(F)(F)CN=C(N)NC=1C=CN(CCCCC#N)N=1 MOEIRUOTENBARR-UHFFFAOYSA-N 0.000 description 2
- IIZHXMZRHOYRGH-UHFFFAOYSA-N 5-(3-aminopyrazol-1-yl)pentanenitrile Chemical compound NC=1C=CN(CCCCC#N)N=1 IIZHXMZRHOYRGH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 229960001380 cimetidine Drugs 0.000 description 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GOXVPASJCHROBY-UHFFFAOYSA-N 1,1,1-trifluoro-2-isothiocyanatoethane Chemical compound FC(F)(F)CN=C=S GOXVPASJCHROBY-UHFFFAOYSA-N 0.000 description 1
- MUBXYDNYFMQNJB-UHFFFAOYSA-N 1-[1-(4-cyanobutyl)pyrazol-3-yl]-3-(2,2,2-trifluoroethyl)thiourea Chemical compound FC(F)(F)CNC(=S)NC=1C=CN(CCCCC#N)N=1 MUBXYDNYFMQNJB-UHFFFAOYSA-N 0.000 description 1
- PUBFHAOQXBRIJT-UHFFFAOYSA-N 5-(5-nitropyrazol-1-yl)pentanenitrile Chemical compound [O-][N+](=O)C1=CC=NN1CCCCC#N PUBFHAOQXBRIJT-UHFFFAOYSA-N 0.000 description 1
- NWWWGAKVHCSAEU-UHFFFAOYSA-N 5-bromopentanenitrile Chemical compound BrCCCCC#N NWWWGAKVHCSAEU-UHFFFAOYSA-N 0.000 description 1
- MZRUFMBFIKGOAL-UHFFFAOYSA-N 5-nitro-1h-pyrazole Chemical compound [O-][N+](=O)C1=CC=NN1 MZRUFMBFIKGOAL-UHFFFAOYSA-N 0.000 description 1
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- -1 [2,2,2-trifluoroethyl]guanidino Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000006870 ms-medium Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8225154 | 1982-09-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO833147L true NO833147L (no) | 1984-03-05 |
Family
ID=10532675
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO833147A NO833147L (no) | 1982-09-03 | 1983-09-02 | Polymorfe forbindelsr, samt fremgangsmaate for fremstilling av slike. |
Country Status (21)
Country | Link |
---|---|
EP (1) | EP0115114B1 (da) |
JP (1) | JPS5965079A (da) |
AT (1) | ATE20740T1 (da) |
AU (1) | AU1789783A (da) |
CA (1) | CA1198734A (da) |
CS (1) | CS236893B2 (da) |
DD (1) | DD211342A5 (da) |
DE (1) | DE3364524D1 (da) |
DK (1) | DK380083D0 (da) |
ES (1) | ES525329A0 (da) |
FI (1) | FI833074A (da) |
GB (1) | GB8320820D0 (da) |
GR (1) | GR78940B (da) |
HU (1) | HU191091B (da) |
IE (1) | IE55805B1 (da) |
IL (1) | IL69533A (da) |
NO (1) | NO833147L (da) |
NZ (1) | NZ205451A (da) |
PT (1) | PT77278B (da) |
SU (1) | SU1237080A3 (da) |
ZA (1) | ZA836196B (da) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8401751D0 (en) * | 1984-01-24 | 1984-02-29 | Ici Plc | Guanidine derivatives |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1233818A (en) * | 1981-03-09 | 1988-03-08 | David J. Gilman | Guanidine derivatives as histamine h-2 receptor antagonists |
-
1983
- 1983-08-02 GB GB838320820A patent/GB8320820D0/en active Pending
- 1983-08-09 IE IE1874/83A patent/IE55805B1/xx unknown
- 1983-08-11 AU AU17897/83A patent/AU1789783A/en not_active Abandoned
- 1983-08-19 DK DK3800/83A patent/DK380083D0/da not_active Application Discontinuation
- 1983-08-21 IL IL69533A patent/IL69533A/xx unknown
- 1983-08-22 ZA ZA836196A patent/ZA836196B/xx unknown
- 1983-08-23 EP EP83304851A patent/EP0115114B1/en not_active Expired
- 1983-08-23 DE DE8383304851T patent/DE3364524D1/de not_active Expired
- 1983-08-23 AT AT83304851T patent/ATE20740T1/de not_active IP Right Cessation
- 1983-08-30 FI FI833074A patent/FI833074A/fi not_active Application Discontinuation
- 1983-08-30 JP JP58157272A patent/JPS5965079A/ja active Pending
- 1983-08-31 HU HU833030A patent/HU191091B/hu unknown
- 1983-09-01 NZ NZ205451A patent/NZ205451A/xx unknown
- 1983-09-01 PT PT77278A patent/PT77278B/pt unknown
- 1983-09-01 GR GR72356A patent/GR78940B/el unknown
- 1983-09-02 DD DD83254489A patent/DD211342A5/de unknown
- 1983-09-02 CS CS836396A patent/CS236893B2/cs unknown
- 1983-09-02 ES ES525329A patent/ES525329A0/es active Granted
- 1983-09-02 CA CA000435933A patent/CA1198734A/en not_active Expired
- 1983-09-02 SU SU833641101A patent/SU1237080A3/ru active
- 1983-09-02 NO NO833147A patent/NO833147L/no unknown
Also Published As
Publication number | Publication date |
---|---|
ES8505738A1 (es) | 1985-06-01 |
AU1789783A (en) | 1984-03-08 |
PT77278A (en) | 1983-10-01 |
ZA836196B (en) | 1984-07-25 |
EP0115114B1 (en) | 1986-07-16 |
NZ205451A (en) | 1985-07-31 |
DE3364524D1 (en) | 1986-08-21 |
DK380083D0 (da) | 1983-08-19 |
CA1198734A (en) | 1985-12-31 |
CS236893B2 (en) | 1985-05-15 |
PT77278B (en) | 1986-03-18 |
SU1237080A3 (ru) | 1986-06-07 |
FI833074A0 (fi) | 1983-08-30 |
GB8320820D0 (en) | 1983-09-01 |
JPS5965079A (ja) | 1984-04-13 |
FI833074A (fi) | 1984-03-04 |
ATE20740T1 (de) | 1986-08-15 |
DD211342A5 (de) | 1984-07-11 |
EP0115114A1 (en) | 1984-08-08 |
IL69533A (en) | 1987-12-31 |
IE831874L (en) | 1984-03-03 |
IE55805B1 (en) | 1991-01-16 |
HU191091B (en) | 1987-01-28 |
GR78940B (da) | 1984-10-02 |
ES525329A0 (es) | 1985-06-01 |
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