NO117078B - - Google Patents

Download PDF

Info

Publication number: NO117078B
Authority: NO; Norway
Prior art keywords: general formula; acid; lower alkyl; compound; inorganic
Prior art date: 1964-06-09

Application number

NO158392A

Other languages

English (en)

Norwegian (no)

Inventor

C Morel

Original Assignee

Geigy Ag J R

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.)

1964-06-09

Filing date

1965-06-08

Publication date

1969-06-30

1965-06-08 Application filed by Geigy Ag J R filed Critical Geigy Ag J R

1969-06-30 Publication of NO117078B publication Critical patent/NO117078B/no

Links

150000001875 compounds Chemical class 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000007522 mineralic acids Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002460 imidazoles Chemical class 0.000 claims description 4
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 claims description 4
235000005985 organic acids Nutrition 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
-1 methoxy- Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical class S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001741 anti-phlogistic effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-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
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
208000025747 Rheumatic disease Diseases 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
229960004365 benzoic acid Drugs 0.000 description 1
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 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
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229960004106 citric acid Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid 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
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
206010034674 peritonitis Diseases 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229940117953 phenylisothiocyanate Drugs 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
108700022737 rat Fat1 Proteins 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/052—Imidazole radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO158392A 1964-06-09 1965-06-08 NO117078B (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH749464A CH436312A (de)	1964-06-09	1964-06-09	Verfahren zur Herstellung von neuen Imidazolderivaten

Publications (1)

Publication Number	Publication Date
NO117078B true NO117078B (fr)	1969-06-30

Family

ID=4325992

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO158392A NO117078B (fr)	1964-06-09	1965-06-08

Country Status (14)

Country	Link
US (1)	US3502650A (fr)
AT (1)	AT249670B (fr)
BE (1)	BE665188A (fr)
BR (1)	BR6570241D0 (fr)
CH (1)	CH436312A (fr)
DE (1)	DE1228615B (fr)
DK (1)	DK108052C (fr)
FI (1)	FI44409C (fr)
FR (2)	FR1450576A (fr)
GB (1)	GB1108180A (fr)
IL (1)	IL23686A (fr)
NL (1)	NL126747C (fr)
NO (1)	NO117078B (fr)
SE (1)	SE324781B (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL124631C (fr) *	1964-06-09

1964
- 1964-06-09 CH CH749464A patent/CH436312A/de unknown
1965
- 1965-06-03 FI FI651327A patent/FI44409C/fi active
- 1965-06-08 AT AT515965A patent/AT249670B/de active
- 1965-06-08 GB GB24083/65A patent/GB1108180A/en not_active Expired
- 1965-06-08 IL IL23686A patent/IL23686A/xx unknown
- 1965-06-08 NL NL6507271A patent/NL126747C/nl active
- 1965-06-08 NO NO158392A patent/NO117078B/no unknown
- 1965-06-08 SE SE7484/65A patent/SE324781B/xx unknown
- 1965-06-08 DE DEG43814A patent/DE1228615B/de active Pending
- 1965-06-08 BR BR170241/65A patent/BR6570241D0/pt unknown
- 1965-06-08 DK DK285265AA patent/DK108052C/da active
- 1965-06-09 BE BE665188A patent/BE665188A/xx unknown
- 1965-06-09 FR FR20003A patent/FR1450576A/fr not_active Expired
- 1965-09-08 FR FR30758A patent/FR5403M/fr not_active Expired
1968
- 1968-03-14 US US712969A patent/US3502650A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NL126747C (fr)	1969-06-16
FI44409C (fi)	1971-11-10
BR6570241D0 (pt)	1973-08-28
US3502650A (en)	1970-03-24
CH436312A (de)	1967-05-31
FR5403M (fr)	1967-09-25
GB1108180A (en)	1968-04-03
IL23686A (en)	1968-11-27
AT249670B (de)	1966-10-25
DE1228615B (de)	1966-11-17
BE665188A (fr)	1965-12-09
DK108052C (da)	1967-08-14
FI44409B (fr)	1971-08-02
NL6507271A (fr)	1965-12-10
FR1450576A (fr)	1966-06-24
SE324781B (fr)	1970-06-15

Publication	Publication Date	Title
DE1695093A1 (de)	1970-12-10	Neue Imidazolderivate
NO139918B (no)	1979-02-26	Nye ioniske jodbenzenderivater for anvendelse i roentgenkontrastmidler
DE1946370B2 (de)	1978-11-09	Substituierte Pyrazol-4-essigsauren, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
US3470195A (en)	1969-09-30	Phenyl and benzyl oxazole acetic acid compounds
NO158432B (no)	1988-05-30	Anordning for feste til gulv.
US2929819A (en)	1960-03-22	New oxazoles
NO121337B (fr)	1971-02-15
US3060177A (en)	1962-10-23	O-(aminoalkyl)oxime derivatives of heterocyclic aldehydes and ketones
US3824271A (en)	1974-07-16	3-alkyl-3-(benzoyl)propionitriles
IE47784B1 (en)	1984-06-13	4-pyridone-3-carboxylic acid derivatives
DK158944B (da)	1990-08-06	Analogifremgangsmaade til fremstilling af substituerede methylimidazolforbindelser
NO129574B (fr)	1974-04-29
US2984668A (en)	1961-05-16	3-(2-hydroxyethyl)-4-methyl-5-phenyloxazolidine and certain esters
Easton et al.	1948	Some isomers of amidone and related compounds
US3178435A (en)	1965-04-13	New pyridinium compounds
US4022782A (en)	1977-05-10	4-Piperazinyl derivatives of pyrazolo [1,5-a]-quinoxaline-3-carboxylic acids and esters
NO743135L (fr)	1975-04-07
JPS584026B2 (ja)	1983-01-24	ピラジンユウドウタイオヨビセイホウ
Isbell et al.	1944	Utilization of Isoamyl α-Methoxyethyl Ketone in the Pfitzinger Synthesis1
US3161647A (en)	1964-12-15	Piperidones
US3592813A (en)	1971-07-13	3-phenyl-9h-pyridazino(3,4-b)indoles
DE1770722A1 (de)	1972-01-13	1,4,9,10-Tetra-benzo[5,6]cyclohepta[1,2-d]4-one und Verfahren zu ihrer Herstellung
US2752352A (en)	1956-06-26	Derivatives of the esters of beta-ketonic acids and process
US4033958A (en)	1977-07-05	4-Morpholino derivatives of pyrazolo[1,5-a]-quinoxaline-3-carboxylic acids and esters
DE1445902C (de)	1972-06-29	Verfahren zur Herstellung von 3-Aminoisoxazolen