NO132761B - - Google Patents

Download PDF

Info

Publication number: NO132761B
Authority: NO; Norway
Prior art keywords: acid; general formula; ethanol; filtered; preparation
Prior art date: 1971-08-24

Application number

NO3013/72A

Other languages

English (en)

Norwegian (no)

Other versions

NO132761C (ja

Inventor

J Baetz

Original Assignee

Seperic

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.)

1971-08-24

Filing date

1972-08-23

Publication date

1975-09-22

1972-08-23 Application filed by Seperic filed Critical Seperic

1975-09-22 Publication of NO132761B publication Critical patent/NO132761B/no

1975-12-29 Publication of NO132761C publication Critical patent/NO132761C/no

Links

150000001875 compounds Chemical class 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 14
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 7
238000010438 heat treatment Methods 0.000 claims description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 6
235000019253 formic acid Nutrition 0.000 claims description 6
229940098779 methanesulfonic acid Drugs 0.000 claims description 6
239000005751 Copper oxide Substances 0.000 claims description 5
229910000431 copper oxide Inorganic materials 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
238000002360 preparation method Methods 0.000 description 17
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
239000000047 product Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical compound NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000000463 material Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000000202 analgesic effect Effects 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
239000000956 alloy Substances 0.000 description 4
229910045601 alloy Inorganic materials 0.000 description 4
LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000003756 stirring Methods 0.000 description 4
230000001476 alcoholic effect Effects 0.000 description 3
IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
-1 2-aminohexahydrobenzothiazole hydrochloride Chemical compound 0.000 description 1
KYUNTDRHCPSMOG-UHFFFAOYSA-N 2h-1,3-benzothiazole-3-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)CSC2=C1 KYUNTDRHCPSMOG-UHFFFAOYSA-N 0.000 description 1
SILRNKZBMNSABG-UHFFFAOYSA-N 4-methyl-4,5-dihydro-1,3-thiazol-2-amine Chemical compound CC1CSC(N)=N1 SILRNKZBMNSABG-UHFFFAOYSA-N 0.000 description 1
IKFLLHVVKJTHAH-UHFFFAOYSA-N 5-methyl-4,5-dihydro-1,3-thiazol-2-amine Chemical compound CC1CN=C(N)S1 IKFLLHVVKJTHAH-UHFFFAOYSA-N 0.000 description 1
LYVYJEYHYALPFP-UHFFFAOYSA-N Cl.N=C1SC(CN1)C1=CC=CC=C1 Chemical compound Cl.N=C1SC(CN1)C1=CC=CC=C1 LYVYJEYHYALPFP-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-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
241000699670 Mus sp. Species 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
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 1
241000219422 Urtica Species 0.000 description 1
235000009108 Urtica dioica Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
Pain & Pain Management (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO3013/72A 1971-08-24 1972-08-23 NO132761C (ja)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3958571A GB1374281A (en)	1971-08-24	1971-08-24	Thiazolino-pyrimidin-5-one derivatives process for their pre paration and applications thereof

Publications (2)

Publication Number	Publication Date
NO132761B true NO132761B (ja)	1975-09-22
NO132761C NO132761C (ja)	1975-12-29

Family

ID=10410359

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO3013/72A NO132761C (ja)	1971-08-24	1972-08-23

Country Status (20)

Country	Link
US (1)	US3876639A (ja)
JP (1)	JPS5518718B2 (ja)
AR (1)	AR204501A1 (ja)
AT (1)	AT318626B (ja)
BE (1)	BE787307A (ja)
CA (1)	CA962677A (ja)
CH (1)	CH540286A (ja)
DE (2)	DE2241241C3 (ja)
DK (1)	DK131470B (ja)
ES (1)	ES406367A1 (ja)
FR (1)	FR2150762B1 (ja)
GB (1)	GB1374281A (ja)
IE (1)	IE36874B1 (ja)
IL (1)	IL40133A (ja)
LU (1)	LU65936A1 (ja)
NL (1)	NL149082B (ja)
NO (1)	NO132761C (ja)
OA (1)	OA04261A (ja)
SE (1)	SE378599B (ja)
ZA (1)	ZA725626B (ja)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4535081A (en) *	1979-11-23	1985-08-13	Pfizer Inc.	Antiallergic and antiulcer 1-oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides and intermediates therefor
US4443451A (en) *	1981-07-15	1984-04-17	Janssen Pharmaceutica N.V.	Bicyclic pyrimidin-5-one derivatives
US4562058A (en) *	1983-08-02	1985-12-31	International Minerals & Chemical Corp.	Process for crystallizing potassium sulfate

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH491944A (de) *	1966-11-29	1970-06-15	Ciba Geigy	Verfahren zur Herstellung von benzheterocyclischen Verbindungen

1971
- 1971-08-24 GB GB3958571A patent/GB1374281A/en not_active Expired
1972
- 1972-01-01 AR AR243711A patent/AR204501A1/es active
- 1972-08-07 CH CH1165672A patent/CH540286A/fr not_active IP Right Cessation
- 1972-08-08 BE BE787307A patent/BE787307A/xx unknown
- 1972-08-10 FR FR7228951A patent/FR2150762B1/fr not_active Expired
- 1972-08-14 US US280165A patent/US3876639A/en not_active Expired - Lifetime
- 1972-08-15 IL IL40133A patent/IL40133A/xx unknown
- 1972-08-15 IE IE1132/72A patent/IE36874B1/xx unknown
- 1972-08-16 ZA ZA725626A patent/ZA725626B/xx unknown
- 1972-08-21 DK DK413472AA patent/DK131470B/da unknown
- 1972-08-21 JP JP8288772A patent/JPS5518718B2/ja not_active Expired
- 1972-08-22 NL NL727211463A patent/NL149082B/xx not_active IP Right Cessation
- 1972-08-22 CA CA149,965A patent/CA962677A/en not_active Expired
- 1972-08-22 LU LU65936A patent/LU65936A1/xx unknown
- 1972-08-22 DE DE19722241241 patent/DE2241241C3/de not_active Expired
- 1972-08-22 DE DE2264979A patent/DE2264979C3/de not_active Expired
- 1972-08-23 AT AT728172A patent/AT318626B/de not_active IP Right Cessation
- 1972-08-23 OA OA54671A patent/OA04261A/xx unknown
- 1972-08-23 ES ES406367A patent/ES406367A1/es not_active Expired
- 1972-08-23 SE SE7210922A patent/SE378599B/xx unknown
- 1972-08-23 NO NO3013/72A patent/NO132761C/no unknown

Also Published As

Publication number	Publication date
JPS4848493A (ja)	1973-07-09
NL7211463A (ja)	1973-02-27
AR204501A1 (es)	1976-02-12
DE2264979A1 (de)	1976-01-15
DE2264979C3 (de)	1981-12-03
NL149082B (nl)	1976-04-15
FR2150762A1 (ja)	1973-04-13
US3876639A (en)	1975-04-08
LU65936A1 (ja)	1973-01-15
FR2150762B1 (ja)	1976-04-16
IL40133A0 (en)	1972-10-29
ZA725626B (en)	1973-05-30
SE378599B (ja)	1975-09-08
DE2264979B2 (de)	1981-02-26
DK131470C (ja)	1975-12-08
GB1374281A (en)	1974-11-20
IL40133A (en)	1975-03-13
DE2241241A1 (de)	1973-03-15
NO132761C (ja)	1975-12-29
JPS5518718B2 (ja)	1980-05-21
DE2241241C3 (de)	1978-01-19
IE36874L (en)	1973-02-24
BE787307A (fr)	1972-12-01
CA962677A (en)	1975-02-11
ES406367A1 (es)	1975-07-01
IE36874B1 (en)	1977-03-16
DK131470B (da)	1975-07-21
DE2241241B2 (de)	1977-06-02
AT318626B (de)	1974-11-11
CH540286A (fr)	1973-08-15
OA04261A (fr)	1979-12-31

Publication	Publication Date	Title
JP2556821B2 (ja)	1996-11-27	三環式芳香族化合物
US4110337A (en)	1978-08-29	Triazolobenzodiazepines
US4161538A (en)	1979-07-17	Substituted phenylacetic acid derivatives and process for the preparation thereof
CA1113114A (en)	1981-11-24	Cycloalkylidenemethylphenylacetic acid derivatives
NO874834L (no)	1988-05-24	Fremgangsmaate for fremstilling av terapeutisk aktive tienopyridinoner.
US4299831A (en)	1981-11-10	2-Trifluoromethyl-3-quinoline carboxamides, analgesic and anti-inflammatory compositions and methods employing them
NO884008L (no)	1989-03-10	Fremgangsmaate for fremstilling av 3,7-diazabicyclo(3,3,1)nonanforbindelser.
HU186523B (en)	1985-08-28	Process for producing quinoline derivatives
US2489236A (en)	1949-11-22	Synthesis of biotin and related compounds
NO147564B (no)	1983-01-24	Analogifremgangsmaate for fremstilling av terapeutisk virksomme 5-benzyol-1,2-dihydro-3h-pyrrolo(1,2-a)pyrrol-1-karboksylsyrederivater
NO132761B (ja)	1975-09-22
Smith Jr et al.	1948	α-Aminophenacylpyridines and Quinolines1
Cannon et al.	1980	Congeners of the. alpha. conformer of dopamine derived from octahydrobenz [h] isoquinoline
US4127720A (en)	1978-11-28	Pyrimido[2,1-a]isoquinoline derivatives having antiallergy activity
US3627763A (en)	1971-12-14	Substituted 2-benzyl-benzofuran derivatives
US3972994A (en)	1976-08-03	Disubstituted azabicycloalkanes
US4232160A (en)	1980-11-04	Isoquinoline propionamides exhibiting analgesic properties
Cadby et al.	1973	Acetylenic Acids. I. The reaction of arylpropiolic acids with carbodiimides
US4576953A (en)	1986-03-18	Quinoline derivatives
US4267331A (en)	1981-05-12	Process for the production of 2-substituted pyrido[4,3-b]-indoles
EP0011206B1 (en)	1983-01-19	9,10-dihydro-4h-benzo(4,5)cyclohepta(1,2-b)thiophen-4,9 imines, process for their preparation and pharmaceutical compositions containing them
US3433794A (en)	1969-03-18	Certain 7 - (2 - aminophenyl) - 4,5 - dihydro thieno(2,3-c)pyridines and derivatives thereof
US3743659A (en)	1973-07-03	Substituted isochromans and processes therefor
NO751401L (ja)	1975-10-23
Lloyd et al.	1954	Synthesis of Oxindole-3-propionic Acid by Ring Rearrangement