DD148215A5 - Verfahren zur herstellung von bicyclo eckige klammer auf 3.1.0 eckige klammer zu hexyl-substituierten carbonylaminophenoxyverbindungen - Google Patents

Verfahren zur herstellung von bicyclo eckige klammer auf 3.1.0 eckige klammer zu hexyl-substituierten carbonylaminophenoxyverbindungen Download PDF

Info

Publication number: DD148215A5
Authority: DD; German Democratic Republic
Prior art keywords: compounds; formula; endobicyclo; phenoxy; compound
Prior art date: 1978-07-03

Application number

DD79214074A

Other languages

German (de)

English (en)

Inventor

Karl G Untch

Belig M Berkoz

Stefan H Unger

Original Assignee

Syntex Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-07-03

Filing date

1979-07-03

Publication date

1981-05-13

1979-07-03 Application filed by Syntex Inc filed Critical Syntex Inc

1981-05-13 Publication of DD148215A5 publication Critical patent/DD148215A5/de

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 125
238000004519 manufacturing process Methods 0.000 title description 2
-1 Hexyl-substituted carbonylaminophenoxy compounds Chemical class 0.000 claims abstract description 66
150000003839 salts Chemical class 0.000 claims abstract description 34
238000000034 method Methods 0.000 claims abstract description 25
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 20
238000002360 preparation method Methods 0.000 claims abstract description 16
150000002431 hydrogen Chemical class 0.000 claims abstract description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
230000008569 process Effects 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
150000002825 nitriles Chemical class 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims description 6
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 5
239000012458 free base Substances 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 20
206010020772 Hypertension Diseases 0.000 abstract description 9
230000000747 cardiac effect Effects 0.000 abstract description 8
239000003814 drug Substances 0.000 abstract description 8
208000019622 heart disease Diseases 0.000 abstract description 8
241001465754 Metazoa Species 0.000 abstract description 7
208000020446 Cardiac disease Diseases 0.000 abstract description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 2
230000003684 cardiac depression Effects 0.000 abstract description 2
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
101100354192 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) exp5 gene Proteins 0.000 abstract 2
101100242909 Streptococcus pneumoniae (strain ATCC BAA-255 / R6) pbpA gene Proteins 0.000 abstract 1
101100439974 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) clpE gene Proteins 0.000 abstract 1
230000009257 reactivity Effects 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 41
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
239000000203 mixture Substances 0.000 description 30
239000000243 solution Substances 0.000 description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000001294 propane Substances 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000543 intermediate Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
238000002474 experimental method Methods 0.000 description 11
239000000047 product Substances 0.000 description 11
239000002876 beta blocker Substances 0.000 description 10
229940097320 beta blocking agent Drugs 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
GOPUCFKUFOFEIC-UHFFFAOYSA-N 2-methyl-1,3-oxazolidine Chemical compound CC1NCCO1 GOPUCFKUFOFEIC-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
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PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 6
239000002585 base Substances 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 5
206010002383 Angina Pectoris Diseases 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000010410 layer Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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 4
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
208000010412 Glaucoma Diseases 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000003973 alkyl amines Chemical class 0.000 description 3
206010003119 arrhythmia Diseases 0.000 description 3
208000006673 asthma Diseases 0.000 description 3
102000012740 beta Adrenergic Receptors Human genes 0.000 description 3
108010079452 beta Adrenergic Receptors Proteins 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
125000002837 carbocyclic group Chemical group 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
238000009472 formulation Methods 0.000 description 3
229960001340 histamine Drugs 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
238000002955 isolation Methods 0.000 description 3
229940039009 isoproterenol Drugs 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
229910052987 metal hydride Inorganic materials 0.000 description 3
150000004681 metal hydrides Chemical class 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
230000000069 prophylactic effect Effects 0.000 description 3
229960003712 propranolol Drugs 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
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125000001424 substituent group Chemical group 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 description 2
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
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IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
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125000005281 alkyl ureido group Chemical group 0.000 description 2
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
239000003849 aromatic solvent Substances 0.000 description 2
125000002619 bicyclic group Chemical group 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000002688 maleic acid derivatives Chemical class 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
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ZYZQSCWSPFLAFM-UHFFFAOYSA-N 4-amino-2-chlorophenol Chemical compound NC1=CC=C(O)C(Cl)=C1 ZYZQSCWSPFLAFM-UHFFFAOYSA-N 0.000 description 1
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
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229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
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DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 description 1
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235000017557 sodium bicarbonate Nutrition 0.000 description 1
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229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
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235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- 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
- 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
- A61P9/06—Antiarrhythmics
- 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
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/132—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing rings
- C07C53/136—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing rings containing condensed ring systems
- 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
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Public Health (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)
Animal Behavior & Ethology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Ophthalmology & Optometry (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD79214074A 1978-07-03 1979-07-03 Verfahren zur herstellung von bicyclo eckige klammer auf 3.1.0 eckige klammer zu hexyl-substituierten carbonylaminophenoxyverbindungen DD148215A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/921,371 US4177280A (en)	1978-07-03	1978-07-03	Bicyclo[3.1.0]hexyl-substituted carbonylaminophenoxy cardiovascular agents

Publications (1)

Publication Number	Publication Date
DD148215A5 true DD148215A5 (de)	1981-05-13

Family

ID=25445332

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79214074A DD148215A5 (de)	1978-07-03	1979-07-03	Verfahren zur herstellung von bicyclo eckige klammer auf 3.1.0 eckige klammer zu hexyl-substituierten carbonylaminophenoxyverbindungen

Country Status (13)

Country	Link
US (1)	US4177280A (da)
EP (1)	EP0007710A1 (da)
JP (1)	JPS559074A (da)
AU (1)	AU4852379A (da)
CA (1)	CA1105054A (da)
DD (1)	DD148215A5 (da)
DK (1)	DK276479A (da)
ES (1)	ES482075A1 (da)
IL (1)	IL57705A0 (da)
NZ (1)	NZ190880A (da)
PL (1)	PL116994B1 (da)
SU (1)	SU854271A3 (da)
ZA (1)	ZA793292B (da)

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US4402976A (en) *	1981-04-24	1983-09-06	E. R. Squibb & Sons, Inc.	Method for treating glaucoma with systemic nadolol compositions
DE3887544T2 (de) *	1987-03-09	1994-06-01	Procter & Gamble	Beta-aminoethyl-substituierte Phenyl-Verbindungen, diese enthaltende entzündungshemmende oder analgetische Zusammensetzungen.
AU2002322720B2 (en)	2001-07-25	2008-11-13	Raptor Pharmaceutical Inc.	Compositions and methods for modulating blood-brain barrier transport
CA2789262C (en)	2005-04-28	2016-10-04	Proteus Digital Health, Inc.	Pharma-informatics system
EP2063905B1 (en)	2006-09-18	2014-07-30	Raptor Pharmaceutical Inc	Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates
TR201908314T4 (tr)	2009-02-20	2019-06-21	2 Bbb Medicines B V	Glutatyon bazlı ilaç dağıtım sistemi.
KR101909711B1 (ko)	2009-05-06	2018-12-19	라보라토리 스킨 케어, 인크.	활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법
US20120077778A1 (en)	2010-09-29	2012-03-29	Andrea Bourdelais	Ladder-Frame Polyether Conjugates
CA3047002A1 (en) *	2017-01-17	2018-07-26	Board Of Regents, The University Of Texas System	Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase
WO2020018670A1 (en)	2018-07-17	2020-01-23	Board Of Regents, The University Of Texas System	Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase

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GB1078852A (en) *	1964-09-30	1967-08-09	Ici Ltd	Alkanolamine derivatives
US4038313A (en) *	1970-01-08	1977-07-26	Ciba-Geigy Corporation	Cycloalkylureido phenoxy propanolamines
CA1149819A (en) *	1970-01-08	1983-07-12	Max Wilhelm	Process for the manufacture of new amines
US4038414A (en) *	1972-06-08	1977-07-26	Ciba-Geigy Corporation	Amines and processes for their manufacture
US4035420A (en) *	1972-07-06	1977-07-12	Aktiebolaget Hassle	Substituted ureido alkylene phenoxy propanolamines
AT334385B (de) *	1973-12-20	1976-01-10	Chemie Linz Ag	Verfahren zur herstellung von neuen phenoxypropylaminderivaten und deren salzen
US4063025A (en) *	1975-02-05	1977-12-13	Yamanouchi Pharmaceutical Co., Ltd.	4-Substituted amino-α-aminomethylbenzyl alcohol derivatives
US4064258A (en) *	1976-07-19	1977-12-20	Syntex (U.S.A.) Inc.	Thiazole cardiovascular agents

1978
- 1978-07-03 US US05/921,371 patent/US4177280A/en not_active Expired - Lifetime
1979
- 1979-06-27 PL PL1979216661A patent/PL116994B1/pl unknown
- 1979-06-29 EP EP79301262A patent/EP0007710A1/en not_active Withdrawn
- 1979-06-29 JP JP8153979A patent/JPS559074A/ja active Pending
- 1979-06-29 DK DK276479A patent/DK276479A/da not_active Application Discontinuation
- 1979-06-29 CA CA331,064A patent/CA1105054A/en not_active Expired
- 1979-06-29 ES ES482075A patent/ES482075A1/es not_active Expired
- 1979-06-29 AU AU48523/79A patent/AU4852379A/en not_active Abandoned
- 1979-06-29 NZ NZ190880A patent/NZ190880A/xx unknown
- 1979-07-02 SU SU792788053A patent/SU854271A3/ru active
- 1979-07-02 IL IL57705A patent/IL57705A0/xx unknown
- 1979-07-03 DD DD79214074A patent/DD148215A5/de unknown
- 1979-07-03 ZA ZA793292A patent/ZA793292B/xx unknown

Also Published As

Publication number	Publication date
AU4852379A (en)	1980-01-10
IL57705A0 (en)	1979-11-30
DK276479A (da)	1980-01-04
EP0007710A1 (en)	1980-02-06
ES482075A1 (es)	1980-03-01
PL116994B1 (en)	1981-07-31
CA1105054A (en)	1981-07-14
JPS559074A (en)	1980-01-22
PL216661A1 (da)	1980-03-24
SU854271A3 (ru)	1981-08-07
NZ190880A (en)	1981-04-24
ZA793292B (en)	1981-02-25
US4177280A (en)	1979-12-04

Publication	Publication Date	Title
CH493463A (de)	1970-07-15	Verfahren zur Herstellung von Naphtalinderivaten
EP0253327B1 (de)	1992-05-06	Neue Diphenylpropylamin-Derivate, ihre Herstellung sowie ihre pharmazeutische Verwendung
DD202001A5 (de)	1983-08-24	Verfahren zur herstellung von aminoaethanolen
DE3609596A1 (de)	1987-10-01	2-azolylmethyl-2-aryl-1,3-dioxolane und deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung
DE2547953A1 (de)	1977-04-28	(1-phenyl-2-triazolyl-aethyl)-aether- derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2743767A1 (de)	1979-04-12	Diastereomere triazolyl-0,n-acetale, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
DD148215A5 (de)	1981-05-13	Verfahren zur herstellung von bicyclo eckige klammer auf 3.1.0 eckige klammer zu hexyl-substituierten carbonylaminophenoxyverbindungen
EP0075207B1 (de)	1986-02-05	Aminopropanolderivate von 2-Hydroxy-beta-phenyl-propiophenonen, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Mittel
EP0365915B1 (de)	1994-04-20	Substituierte 2-Aminothiazole
EP0271013A2 (de)	1988-06-15	Basisch substituierte Phenylacetonitrile, ihre Herstellung und diese enthaltende Arzneimittel
DE2547954C2 (da)	1989-02-16
CH385196A (de)	1964-12-15	Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate
DE2416016A1 (de)	1975-09-25	Neue 1- eckige klammer auf beta-(aminocarbonylphenoxy)-aethylamino eckige klammer zu -3- (thiazol-2-oxy)-2-propanole und ihre derivate
DE3608727A1 (de)	1987-09-17	1,1-disubstituierte cyclopropanderivate, verfahren zu ihrer herstellung sowie ihre verwendung als antimykotika oder als zwischenprodukte
EP0082461B1 (de)	1987-03-04	Substituierte Phenoxyalkanolamine und Phenoxyalkanol-cycloalkylamine, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende pharmazeutische Zubereitungen und Zwischenprodukte
EP0016974A1 (de)	1980-10-15	3-Substituierte Pyridin-Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Fungizide und Zwischenprodukte
CH645368A5 (de)	1984-09-28	2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)benzoesaeure-derivate sowie verfahren zu deren herstellung.
DE2623314A1 (de)	1977-12-08	Neue 1-aryloxy-2-hydroxy-3- aminopropane und verfahren zu ihrer herstellung
EP0027928B1 (de)	1983-03-09	Piperidinderivate von 4,5-Dialkyl-3-hydroxy-pyrrol-2-carbonsäureestern, ihre Herstellung und diese enthaltende pharmazeutische Zubereitungen
DE3609597A1 (de)	1987-10-01	2-azolylmethyl-2-aryl-1,3-dioxolane und deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung
DE2547524A1 (de)	1977-04-28	Disubstituierte phenolaether des 3-amino-2-hydroxypropans, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
CH643250A5 (de)	1984-05-30	(3-alkylamino-2-hydroxypropoxy)-furan-2-carbonsaeureanilide.
DE2137538C3 (de)	1980-10-02	oxyamin und seine Salze sowie ein Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel
EP0037062B1 (de)	1984-10-17	Substituierte 3-Aryl-2-cycloalken-1-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE2540552A1 (de)	1976-03-25	Cycloalkylderivate von 1-aryloxy-3- amino-2-propanolen