CH621330A5 - - Google Patents
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- Publication number
- CH621330A5 CH621330A5 CH606376A CH606376A CH621330A5 CH 621330 A5 CH621330 A5 CH 621330A5 CH 606376 A CH606376 A CH 606376A CH 606376 A CH606376 A CH 606376A CH 621330 A5 CH621330 A5 CH 621330A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- formula
- alkyl
- compounds
- substituted
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- -1 2,3-epoxypropoxy Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- IAOQSFIDUNOKFQ-UHFFFAOYSA-N 1-(tert-butylamino)-3-spiro[1,3-dihydroindene-2,1'-cyclohexane]-4-yloxypropan-2-ol Chemical compound C(C)(C)(C)NCC(COC1=C2CC3(CCCCC3)CC2=CC=C1)O IAOQSFIDUNOKFQ-UHFFFAOYSA-N 0.000 claims 1
- FMRWQLAJBBKXDM-UHFFFAOYSA-N 2,2,5,5-tetramethylpyrrolidine Chemical group CC1(C)CCC(C)(C)N1 FMRWQLAJBBKXDM-UHFFFAOYSA-N 0.000 claims 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical group CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-M malonate(1-) Chemical compound OC(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-M 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000000054 salidiuretic effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- YZXYDDLVLCXGCU-UHFFFAOYSA-N 4-hydroxyspiro[3h-indene-2,1'-cyclohexane]-1-one Chemical compound C1C=2C(O)=CC=CC=2C(=O)C21CCCCC2 YZXYDDLVLCXGCU-UHFFFAOYSA-N 0.000 description 1
- BTYSYELHQDGJAB-UHFFFAOYSA-N 4-methoxy-2,3-dihydroinden-1-one Chemical compound COC1=CC=CC2=C1CCC2=O BTYSYELHQDGJAB-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 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
- 150000007513 acids Chemical class 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 201000010063 epididymitis Diseases 0.000 description 1
- 230000001834 epinephrinelike Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 239000007788 liquid Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000008986 metabolic interaction Effects 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/38—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH606376A CH621330A5 (it) | 1976-05-14 | 1976-05-14 | |
| DE19772719871 DE2719871A1 (de) | 1976-05-14 | 1977-05-04 | Substituierte 3-amino-2-hydroxypropoxyphenyl-derivate, ihre verwendung und herstellung |
| SE7705221A SE7705221L (sv) | 1976-05-14 | 1977-05-05 | Organiska foreningar, deras anvendning och framstellning |
| DK197677A DK197677A (da) | 1976-05-14 | 1977-05-05 | Fremgangsmade til fremstilling af substituerede 1-amino-2-hydroxypropoxyderivater |
| FI771427A FI771427A (it) | 1976-05-14 | 1977-05-05 | |
| NL7705128A NL7705128A (nl) | 1976-05-14 | 1977-05-10 | Werkwijze voor het bereiden en toepassen van aromatische verbindingen. |
| US05/795,439 US4322437A (en) | 1976-05-14 | 1977-05-10 | Spiro substituted indanones and tetralones |
| CY1226A CY1226A (en) | 1976-05-14 | 1977-05-10 | Spirocyclic compounds |
| GB19551/77A GB1576034A (en) | 1976-05-14 | 1977-05-10 | Spirocyclic compounds |
| IE971/77A IE44950B1 (en) | 1976-05-14 | 1977-05-12 | Improvements in or relating to spirocyclic compounds |
| BE177524A BE854567A (fr) | 1976-05-14 | 1977-05-12 | Nouveaux derives du propyleneglycol |
| PT66540A PT66540B (fr) | 1976-05-14 | 1977-05-12 | Procede pour la preparation de nouveaux composes organiques a effect pharmaceutique |
| FR7714506A FR2351091A1 (fr) | 1976-05-14 | 1977-05-12 | Nouveaux derives du propyleneglycol, leur preparation et leur application comme medicaments |
| CA278,293A CA1095913A (en) | 1976-05-14 | 1977-05-12 | 3-amino-2-hydroxypropoxyphenyl derivatives |
| NZ184079A NZ184079A (en) | 1976-05-14 | 1977-05-12 | 3-(substituted amino)-2-hydroxypropoxy derivatives of spiro compounds and pharmaceutical compositions |
| IL52072A IL52072A (en) | 1976-05-14 | 1977-05-12 | 4-(or5)-(3-(substituted amino)-2-hydroxypropoxy)-spiro cycloalkane indanone or naphthone derivatives,their preparation and pharmaceutical compositions coprising them |
| ES77458724A ES458724A1 (es) | 1976-05-14 | 1977-05-12 | Procedimiento para la produccion de derivados de 3-amino-2- hidroxi-propoxifenilo. |
| JP5449177A JPS52139051A (en) | 1976-05-14 | 1977-05-13 | Improvement of organic compound |
| AT343577A AT362349B (de) | 1976-05-14 | 1977-05-13 | Verfahren zur herstellung von neuen 3-amino-2- -hydroxypropoxyaryl-derivaten |
| PH19769A PH14176A (en) | 1976-05-14 | 1977-05-13 | 3-amino-2-hydroxypropyl derivative |
| ZA00772873A ZA772873B (en) | 1976-05-14 | 1977-05-13 | Improvements in or relating to organic compounds |
| SU772480276A SU634663A3 (ru) | 1976-05-14 | 1977-05-13 | Способ получени производных индана или их солей, рацематов или оптическиактивных антиподов |
| AU25140/77A AU513066B2 (en) | 1976-05-14 | 1977-05-13 | 3 amino-2hydroxy-propoxphenyl derivatives |
| SG849/83A SG84983G (en) | 1976-05-14 | 1983-12-29 | Improvements in or relating to spirocyclic compounds |
| KE3405A KE3405A (en) | 1976-05-14 | 1984-04-19 | Improvements in or relating to spirocyclic compounds |
| HK359/84A HK35984A (en) | 1976-05-14 | 1984-04-26 | Improvements in or relating to spirocyclic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH606376A CH621330A5 (it) | 1976-05-14 | 1976-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621330A5 true CH621330A5 (it) | 1981-01-30 |
Family
ID=4303639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH606376A CH621330A5 (it) | 1976-05-14 | 1976-05-14 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4322437A (it) |
| JP (1) | JPS52139051A (it) |
| AT (1) | AT362349B (it) |
| AU (1) | AU513066B2 (it) |
| BE (1) | BE854567A (it) |
| CA (1) | CA1095913A (it) |
| CH (1) | CH621330A5 (it) |
| CY (1) | CY1226A (it) |
| DE (1) | DE2719871A1 (it) |
| DK (1) | DK197677A (it) |
| ES (1) | ES458724A1 (it) |
| FI (1) | FI771427A (it) |
| FR (1) | FR2351091A1 (it) |
| GB (1) | GB1576034A (it) |
| HK (1) | HK35984A (it) |
| IE (1) | IE44950B1 (it) |
| IL (1) | IL52072A (it) |
| KE (1) | KE3405A (it) |
| NL (1) | NL7705128A (it) |
| NZ (1) | NZ184079A (it) |
| PH (1) | PH14176A (it) |
| PT (1) | PT66540B (it) |
| SE (1) | SE7705221L (it) |
| SG (1) | SG84983G (it) |
| SU (1) | SU634663A3 (it) |
| ZA (1) | ZA772873B (it) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2810869A1 (de) * | 1977-03-24 | 1978-09-28 | Sandoz Ag | 3-amino-2-hydroxypropoxy-derivate, ihre herstellung und verwendung |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2641152A (en) * | 1949-07-15 | 1953-06-09 | Herbert M Hise | Stringed musical instrument |
| GB1046001A (en) * | 1964-03-12 | 1966-10-19 | Ici Ltd | Propanolamine derivatives |
| US3839415A (en) * | 1965-10-22 | 1974-10-01 | Lilly Co Eli | 2-halo-1-(alkyl-1-(alkylamino)ethyl)vinyl benzoic acid esters and derivatives |
| US3641152A (en) * | 1968-09-23 | 1972-02-08 | Warner Lambert Pharmaceutical | 3 4-dihydronaphthalenoneoxy-2-hydroxy-propylamines |
| CH554314A (de) * | 1969-06-03 | 1974-09-30 | Sandoz Ag | Verfahren zur herstellung neuer fluorenone. |
| BE755071A (fr) * | 1969-09-17 | 1971-02-22 | Warner Lambert Pharmaceutical | Procede de resolution de la dl-5-/3-(terbutylamino)-2- hydroxy-propoxy/-3,4-dihydro-1(2h) naphtalenone |
-
1976
- 1976-05-14 CH CH606376A patent/CH621330A5/de not_active IP Right Cessation
-
1977
- 1977-05-04 DE DE19772719871 patent/DE2719871A1/de not_active Ceased
- 1977-05-05 SE SE7705221A patent/SE7705221L/xx not_active Application Discontinuation
- 1977-05-05 DK DK197677A patent/DK197677A/da not_active Application Discontinuation
- 1977-05-05 FI FI771427A patent/FI771427A/fi not_active Application Discontinuation
- 1977-05-10 US US05/795,439 patent/US4322437A/en not_active Expired - Lifetime
- 1977-05-10 GB GB19551/77A patent/GB1576034A/en not_active Expired
- 1977-05-10 CY CY1226A patent/CY1226A/xx unknown
- 1977-05-10 NL NL7705128A patent/NL7705128A/xx not_active Application Discontinuation
- 1977-05-12 ES ES77458724A patent/ES458724A1/es not_active Expired
- 1977-05-12 FR FR7714506A patent/FR2351091A1/fr active Granted
- 1977-05-12 BE BE177524A patent/BE854567A/xx not_active IP Right Cessation
- 1977-05-12 CA CA278,293A patent/CA1095913A/en not_active Expired
- 1977-05-12 NZ NZ184079A patent/NZ184079A/xx unknown
- 1977-05-12 PT PT66540A patent/PT66540B/pt unknown
- 1977-05-12 IE IE971/77A patent/IE44950B1/en unknown
- 1977-05-12 IL IL52072A patent/IL52072A/xx unknown
- 1977-05-13 SU SU772480276A patent/SU634663A3/ru active
- 1977-05-13 JP JP5449177A patent/JPS52139051A/ja active Pending
- 1977-05-13 ZA ZA00772873A patent/ZA772873B/xx unknown
- 1977-05-13 AU AU25140/77A patent/AU513066B2/en not_active Expired
- 1977-05-13 PH PH19769A patent/PH14176A/en unknown
- 1977-05-13 AT AT343577A patent/AT362349B/de not_active IP Right Cessation
-
1983
- 1983-12-29 SG SG849/83A patent/SG84983G/en unknown
-
1984
- 1984-04-19 KE KE3405A patent/KE3405A/xx unknown
- 1984-04-26 HK HK359/84A patent/HK35984A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PH14176A (en) | 1981-03-19 |
| JPS52139051A (en) | 1977-11-19 |
| CY1226A (en) | 1984-04-06 |
| SG84983G (en) | 1985-01-11 |
| GB1576034A (en) | 1980-10-01 |
| PT66540B (fr) | 1979-10-22 |
| BE854567A (fr) | 1977-11-14 |
| KE3405A (en) | 1985-02-01 |
| FR2351091B1 (it) | 1980-01-18 |
| FI771427A (it) | 1977-11-15 |
| FR2351091A1 (fr) | 1977-12-09 |
| NL7705128A (nl) | 1977-11-16 |
| ATA343577A (de) | 1980-10-15 |
| SE7705221L (sv) | 1977-11-15 |
| HK35984A (en) | 1984-05-04 |
| PT66540A (fr) | 1977-06-01 |
| IE44950L (en) | 1977-11-14 |
| ZA772873B (en) | 1978-12-27 |
| IL52072A (en) | 1980-10-26 |
| IL52072A0 (en) | 1977-07-31 |
| CA1095913A (en) | 1981-02-17 |
| IE44950B1 (en) | 1982-05-19 |
| US4322437A (en) | 1982-03-30 |
| AU2514077A (en) | 1978-11-16 |
| AT362349B (de) | 1981-05-11 |
| NZ184079A (en) | 1978-09-25 |
| DK197677A (da) | 1977-11-15 |
| DE2719871A1 (de) | 1977-12-01 |
| AU513066B2 (en) | 1980-11-13 |
| ES458724A1 (es) | 1978-08-01 |
| SU634663A3 (ru) | 1978-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |