NO801131L - Fremgangsmaate for fremstilling av oksazolin- og tiazolin- derivater med hypoglykemisk aktivitet - Google Patents
Fremgangsmaate for fremstilling av oksazolin- og tiazolin- derivater med hypoglykemisk aktivitetInfo
- Publication number
- NO801131L NO801131L NO801131A NO801131A NO801131L NO 801131 L NO801131 L NO 801131L NO 801131 A NO801131 A NO 801131A NO 801131 A NO801131 A NO 801131A NO 801131 L NO801131 L NO 801131L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- phenyl
- formula
- halogen
- optionally substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 230000000694 effects Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 150000002367 halogens Chemical class 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052717 sulfur Chemical group 0.000 claims abstract description 8
- 239000011593 sulfur Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- -1 nitro- Chemical class 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims 1
- 230000002218 hypoglycaemic effect Effects 0.000 abstract description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
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- 239000002904 solvent Substances 0.000 description 9
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- 239000000203 mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
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- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
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- 239000013067 intermediate product Substances 0.000 description 2
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- 150000002540 isothiocyanates Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical class CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 2
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- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
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- OKIWPJMZQPGMKZ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(3-methyl-1,3-thiazol-2-ylidene)thiourea Chemical compound CN1C=CSC1=NC(=S)NC1=CC=C(Cl)C=C1 OKIWPJMZQPGMKZ-UHFFFAOYSA-N 0.000 description 1
- KATJXPBACMFWMO-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-(3-methyl-1,3-thiazol-2-ylidene)thiourea Chemical compound CN1C=CSC1=NC(=S)NC1=CC=C(F)C=C1 KATJXPBACMFWMO-UHFFFAOYSA-N 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 229920000609 methyl cellulose Polymers 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- WCUWHUUPGXCMMQ-UHFFFAOYSA-N morpholine-4-carboximidamide Chemical compound NC(=N)N1CCOCC1 WCUWHUUPGXCMMQ-UHFFFAOYSA-N 0.000 description 1
- CECRNQLNRGDJNB-UHFFFAOYSA-N n'-(4-fluorophenyl)-n-(3-methyl-1,3-thiazol-2-ylidene)morpholine-4-carboximidamide Chemical compound CN1C=CSC1=NC(N1CCOCC1)=NC1=CC=C(F)C=C1 CECRNQLNRGDJNB-UHFFFAOYSA-N 0.000 description 1
- CBJSSZSJRLHWHJ-UHFFFAOYSA-N n'-(4-methylphenyl)-n-(3-methyl-1,3-thiazol-2-ylidene)morpholine-4-carboximidamide;hydroiodide Chemical compound I.C1=CC(C)=CC=C1N=C(N1CCOCC1)N=C1N(C)C=CS1 CBJSSZSJRLHWHJ-UHFFFAOYSA-N 0.000 description 1
- WGZLKRJADDAQJH-UHFFFAOYSA-N n'-phenyl-n-(3,4,5-trimethyl-1,3-thiazol-2-ylidene)morpholine-4-carboximidamide Chemical compound CN1C(C)=C(C)SC1=NC(N1CCOCC1)=NC1=CC=CC=C1 WGZLKRJADDAQJH-UHFFFAOYSA-N 0.000 description 1
- CLQUGHFWJNDIOA-UHFFFAOYSA-N n-(3-ethyl-1,3-thiazol-2-ylidene)-n'-phenylmorpholine-4-carboximidamide Chemical compound CCN1C=CSC1=NC(N1CCOCC1)=NC1=CC=CC=C1 CLQUGHFWJNDIOA-UHFFFAOYSA-N 0.000 description 1
- FXWHRMBOGXRRPV-UHFFFAOYSA-N n-(3-methyl-1,3-benzothiazol-2-ylidene)-n'-phenylmorpholine-4-carboximidamide;hydrochloride Chemical compound Cl.CN1C2=CC=CC=C2SC1=NC(N1CCOCC1)=NC1=CC=CC=C1 FXWHRMBOGXRRPV-UHFFFAOYSA-N 0.000 description 1
- JBFFCPAXYNVLGM-UHFFFAOYSA-N n-(3-methyl-1,3-benzothiazol-2-ylidene)-n'-phenylpyrrolidine-1-carboximidamide Chemical compound CN1C2=CC=CC=C2SC1=NC(N1CCCC1)=NC1=CC=CC=C1 JBFFCPAXYNVLGM-UHFFFAOYSA-N 0.000 description 1
- OXJLJONTORNWKV-UHFFFAOYSA-N n-(3-methyl-1,3-thiazol-2-ylidene)-n'-phenylmorpholine-4-carboximidamide;hydroiodide Chemical compound I.CN1C=CSC1=NC(N1CCOCC1)=NC1=CC=CC=C1 OXJLJONTORNWKV-UHFFFAOYSA-N 0.000 description 1
- RWTZVOOEWBZWQZ-UHFFFAOYSA-N n-(3-methyl-1,3-thiazol-2-ylidene)-n'-phenylpyrrolidine-1-carboximidamide Chemical compound CN1C=CSC1=NC(N1CCCC1)=NC1=CC=CC=C1 RWTZVOOEWBZWQZ-UHFFFAOYSA-N 0.000 description 1
- AZBQGGZPYLKYNN-UHFFFAOYSA-N n-(5-bromo-3-methyl-1,3-thiazol-2-ylidene)-n'-phenylmorpholine-4-carboximidamide;hydrochloride Chemical compound Cl.CN1C=C(Br)SC1=NC(N1CCOCC1)=NC1=CC=CC=C1 AZBQGGZPYLKYNN-UHFFFAOYSA-N 0.000 description 1
- AYOOGWWGECJQPI-NSHDSACASA-N n-[(1s)-1-(5-fluoropyrimidin-2-yl)ethyl]-3-(3-propan-2-yloxy-1h-pyrazol-5-yl)imidazo[4,5-b]pyridin-5-amine Chemical compound N1C(OC(C)C)=CC(N2C3=NC(N[C@@H](C)C=4N=CC(F)=CN=4)=CC=C3N=C2)=N1 AYOOGWWGECJQPI-NSHDSACASA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 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
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
- Peptides Or Proteins (AREA)
- Luminescent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7913864 | 1979-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO801131L true NO801131L (no) | 1980-10-21 |
Family
ID=10504680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO801131A NO801131L (no) | 1979-04-20 | 1980-04-18 | Fremgangsmaate for fremstilling av oksazolin- og tiazolin- derivater med hypoglykemisk aktivitet |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4409216A (de) |
| EP (1) | EP0018107B1 (de) |
| JP (1) | JPS55141474A (de) |
| AT (1) | ATE2075T1 (de) |
| AU (1) | AU5758880A (de) |
| DE (1) | DE3061396D1 (de) |
| DK (1) | DK167580A (de) |
| ES (2) | ES8105306A1 (de) |
| FI (1) | FI801253A (de) |
| GR (1) | GR67301B (de) |
| IE (1) | IE49697B1 (de) |
| IL (1) | IL59803A0 (de) |
| NO (1) | NO801131L (de) |
| ZA (1) | ZA801970B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2075805B1 (es) * | 1993-12-30 | 1996-10-16 | Univ Murcia | Procedimiento para la obtencion de iminooxazolinas n-n'-sustituidas. |
| DE102004008141A1 (de) * | 2004-02-19 | 2005-09-01 | Abbott Gmbh & Co. Kg | Guanidinverbindungen und ihre Verwendung als Bindungspartner für 5-HT5-Rezeptoren |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3023103A (en) * | 1960-08-02 | 1962-02-27 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsions |
| DE2205744A1 (de) | 1972-02-08 | 1973-08-09 | Thomae Gmbh Dr K | Neue durch einen guanidinylidenrest substituierte heterocyclen und verfahren zu ihrer herstellung |
| NZ183570A (en) * | 1976-03-19 | 1979-06-08 | Mcneilab Inc | Heterocyclic guanidine derivatives, having anti-secretory and hypogliycaemic activity |
| CS225804B2 (cs) | 1976-03-19 | 1984-02-13 | Mcneilab Inc | Způsob výroby heterocyklických derivátů guanidinu |
| US4089965A (en) * | 1976-03-26 | 1978-05-16 | American Cyanamid Company | Thiazolylphenylguanidines as antirhinovirus agents |
| CA1201119A (en) * | 1978-09-18 | 1986-02-25 | Mcneilab, Inc. | Diaza-cyclic derivatives of guanidine |
| AU5263779A (en) * | 1978-11-29 | 1980-05-29 | Beecham Group Limited | Derivatives of thiazolidin-2-ylidene and oxazolidin-2-ylidene with hypoglycaemic acitivity |
-
1980
- 1980-03-27 EP EP80300949A patent/EP0018107B1/de not_active Expired
- 1980-03-27 AT AT80300949T patent/ATE2075T1/de active
- 1980-03-27 DE DE8080300949T patent/DE3061396D1/de not_active Expired
- 1980-04-02 ZA ZA00801970A patent/ZA801970B/xx unknown
- 1980-04-10 IL IL59803A patent/IL59803A0/xx unknown
- 1980-04-11 US US06/139,284 patent/US4409216A/en not_active Expired - Lifetime
- 1980-04-15 GR GR61687A patent/GR67301B/el unknown
- 1980-04-17 ES ES490675A patent/ES8105306A1/es not_active Expired
- 1980-04-18 AU AU57588/80A patent/AU5758880A/en not_active Abandoned
- 1980-04-18 NO NO801131A patent/NO801131L/no unknown
- 1980-04-18 DK DK167580A patent/DK167580A/da active IP Right Grant
- 1980-04-18 FI FI801253A patent/FI801253A/fi not_active Application Discontinuation
- 1980-04-18 JP JP5155880A patent/JPS55141474A/ja active Pending
- 1980-04-18 IE IE787/80A patent/IE49697B1/en unknown
- 1980-12-09 ES ES497560A patent/ES497560A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES8200668A1 (es) | 1981-11-16 |
| IE49697B1 (en) | 1985-11-27 |
| US4409216A (en) | 1983-10-11 |
| ES497560A0 (es) | 1981-11-16 |
| GR67301B (de) | 1981-06-29 |
| EP0018107B1 (de) | 1982-12-22 |
| ZA801970B (en) | 1981-04-29 |
| EP0018107A1 (de) | 1980-10-29 |
| DK167580A (da) | 1980-10-21 |
| JPS55141474A (en) | 1980-11-05 |
| ES490675A0 (es) | 1981-05-16 |
| IE800787L (en) | 1980-10-20 |
| ATE2075T1 (de) | 1983-01-15 |
| FI801253A (fi) | 1980-10-21 |
| DE3061396D1 (en) | 1983-01-27 |
| ES8105306A1 (es) | 1981-05-16 |
| AU5758880A (en) | 1980-10-23 |
| IL59803A0 (en) | 1980-06-30 |
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