NO891898L - Fremgangsmaate ved fremstilling av naftotiazepinoner. - Google Patents

Fremgangsmaate ved fremstilling av naftotiazepinoner.

Info

Publication number: NO891898L
Authority: NO; Norway
Prior art keywords: acid; hydroxy; thio; amino; naphthalenyl
Prior art date: 1988-05-10

Application number

NO89891898A

Other languages

English (en)

Norwegian (no)

Other versions

NO891898D0 (no

Inventor

Erno Mohacsi

Original Assignee

Hoffmann La Roche

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.)

1988-05-10

Filing date

1989-05-09

Publication date

1989-11-13

1989-05-09 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1989-05-09 Publication of NO891898D0 publication Critical patent/NO891898D0/no

1989-11-13 Publication of NO891898L publication Critical patent/NO891898L/no

Links

238000000034 method Methods 0.000 title claims description 24
238000004519 manufacturing process Methods 0.000 title 1
-1 2-amino-1-naphthalenyl Chemical group 0.000 claims description 66
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 51
150000001875 compounds Chemical class 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 23
FLPQWEDKJCCQKB-UHFFFAOYSA-N 4-(1,2,3,4,5,6,7,8-octahydroisoquinolin-1-ylmethyl)phenol Chemical compound C1=CC(O)=CC=C1CC1C(CCCC2)=C2CCN1 FLPQWEDKJCCQKB-UHFFFAOYSA-N 0.000 claims description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 18
238000000926 separation method Methods 0.000 claims description 15
LUXPJWFSGRUPTP-UHFFFAOYSA-N 4-(1,2,3,4,5,6,7,8-octahydroisoquinolin-1-ylmethyl)phenol;hydrate Chemical compound O.C1=CC(O)=CC=C1CC1C(CCCC2)=C2CCN1 LUXPJWFSGRUPTP-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 11
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 claims description 10
238000011084 recovery Methods 0.000 claims description 10
150000007522 mineralic acids Chemical class 0.000 claims description 9
238000001953 recrystallisation Methods 0.000 claims description 9
239000012043 crude product Substances 0.000 claims description 8
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
239000000908 ammonium hydroxide Substances 0.000 claims description 7
238000001914 filtration Methods 0.000 claims description 6
238000002955 isolation Methods 0.000 claims description 6
QOVOTVDVYPNWOH-UHFFFAOYSA-N 5h-benzo[i][1,5]benzothiazepin-4-one Chemical compound S1C=CC(=O)NC2=CC=C(C=CC=C3)C3=C21 QOVOTVDVYPNWOH-UHFFFAOYSA-N 0.000 claims description 5
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000000605 extraction Methods 0.000 claims description 2
239000012452 mother liquor Substances 0.000 claims description 2
238000000746 purification Methods 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000000725 suspension Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
239000000203 mixture Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 5
238000003776 cleavage reaction Methods 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000000523 sample Substances 0.000 description 5
230000007017 scission Effects 0.000 description 5
125000001589 carboacyl group Chemical group 0.000 description 4
125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000002024 ethyl acetate extract Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
239000008096 xylene Substances 0.000 description 3
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
239000003849 aromatic solvent Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 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 description 2
IGSREHOALYQNPA-YADHBBJMSA-N (2s,3s)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydrobenzo[i][1,5]benzothiazepin-4-one Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](O)C(=O)N(CCN(C)C)C(C=CC=2C3=CC=CC=2)=C3S1 IGSREHOALYQNPA-YADHBBJMSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
LRGZZEOWQURWFK-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydroisoquinoline Chemical compound C1NCCC2CCCC=C21 LRGZZEOWQURWFK-UHFFFAOYSA-N 0.000 description 1
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
CRUWGMMAJMCGJX-UHFFFAOYSA-N 5h-thiazepin-4-one Chemical compound O=C1CC=CSN=C1 CRUWGMMAJMCGJX-UHFFFAOYSA-N 0.000 description 1
229940127291 Calcium channel antagonist Drugs 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000000480 calcium channel blocker Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000012716 precipitator Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/26—Separation; Purification; Stabilisation; Use of additives
- C07C319/28—Separation; Purification
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
Paper (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO89891898A 1988-05-10 1989-05-09 Fremgangsmaate ved fremstilling av naftotiazepinoner. NO891898L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/192,252 US4864058A (en)	1988-05-10	1988-05-10	Process for making optically active naphtho[1,2-b][1,4]thiazepin-4(5H)-ones

Publications (2)

Publication Number	Publication Date
NO891898D0 NO891898D0 (no)	1989-05-09
NO891898L true NO891898L (no)	1989-11-13

Family

ID=22708895

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO89891898A NO891898L (no)	1988-05-10	1989-05-09	Fremgangsmaate ved fremstilling av naftotiazepinoner.

Country Status (8)

Country	Link
US (1)	US4864058A (da)
EP (1)	EP0341562A1 (da)
JP (1)	JPH0215056A (da)
DK (1)	DK184789A (da)
FI (1)	FI892221A (da)
NO (1)	NO891898L (da)
PT (1)	PT90503A (da)
YU (1)	YU95089A (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5008411A (en) *	1988-05-24	1991-04-16	Hoffmann-La Roche Inc.	Glycidic acid ester and process of preparation
IT1240651B (it) *	1990-05-17	1993-12-17	Zambon Spa	Processo per la risoluzione di derivati glicidici
US6953919B2 (en) *	2003-01-30	2005-10-11	Thermal Solutions, Inc.	RFID-controlled smart range and method of cooking and heating

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1152721B (it) *	1982-10-15	1987-01-07	Luso Farmaco Inst	Risoluzione ottica dell'acido dl-alfa-2-idrossi-3-(4-metossifenil)-3-(2-amminofeniltio)propionico
US4652561A (en) *	1986-02-26	1987-03-24	Hoffmann-La Roche Inc.	Naphtho[1,2-b]-1,4-thiazepinones

1988
- 1988-05-10 US US07/192,252 patent/US4864058A/en not_active Expired - Fee Related
1989
- 1989-04-17 DK DK184789A patent/DK184789A/da not_active Application Discontinuation
- 1989-05-03 EP EP89107981A patent/EP0341562A1/en not_active Withdrawn
- 1989-05-09 PT PT90503A patent/PT90503A/pt not_active Application Discontinuation
- 1989-05-09 YU YU00950/89A patent/YU95089A/xx unknown
- 1989-05-09 JP JP1114333A patent/JPH0215056A/ja active Pending
- 1989-05-09 NO NO89891898A patent/NO891898L/no unknown
- 1989-05-09 FI FI892221A patent/FI892221A/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
DK184789D0 (da)	1989-04-17
YU95089A (en)	1990-12-31
PT90503A (pt)	1989-11-30
DK184789A (da)	1989-11-11
JPH0215056A (ja)	1990-01-18
EP0341562A1 (en)	1989-11-15
FI892221A (fi)	1989-11-11
FI892221A0 (fi)	1989-05-09
NO891898D0 (no)	1989-05-09
US4864058A (en)	1989-09-05

Publication	Publication Date	Title
KR100428238B1 (ko)	2004-04-30	약리학적 활성 물질의 제조 방법
NO163566B (no)	1990-03-12	1,5-benzothiazepinderivater som er anvendelige som utgangsmaterialer ved fremstilling av nye, terapeutisk aktive 8-klor-1,5-benzothiazepinderivater.
US4416819A (en)	1983-11-22	Process for preparing 1,5-benzothiazephine derivatives
DK154563B (da)	1988-11-28	Fremgangsmaade til fremstilling af en racemisk eller optisk aktiv (+)-thiolacton eller (+)-bioton
CA1272717A (en)	1990-08-14	Naphthothiazepinones
JPH0567136B2 (da)	1993-09-24
US4931587A (en)	1990-06-05	Process for the optical resolution of a racemic acid
JPH05125051A (ja)	1993-05-21	立体構造の均一な置換された（キノリン−２−イル−メトキシ）−フエニル酢酸の合成方法
FR2620700A1 (fr)	1989-03-24	Procede de synthese d'alpha amino acides n alkyles et leurs esters. application a la synthese de carboxyalkyl dipeptides
US4600534A (en)	1986-07-15	Process and intermediates for manufacture of 3-(5-amino-1-carboxypentylamino)-tetrahydro-1-benzazepin-2-one-1-acetic acid
NO891898L (no)	1989-11-13	Fremgangsmaate ved fremstilling av naftotiazepinoner.
EP0204911B1 (en)	1990-06-20	A new process for the optical resolution of racemic mixtures of alpha-naphthylpropionic acids
US3978085A (en)	1976-08-31	Process for benz[f]-2,5-oxazocines
US4996352A (en)	1991-02-26	Enantiomers of β-[(2-amino-1-naphthalenyl) thiol]-α-hydroxy-4-methoxybenzene propanoic acid
US5225557A (en)	1993-07-06	Process for making optically active naphtho[1,2-b]thiazepin-4(5H)-ones
US4885364A (en)	1989-12-05	Resolution process for benzazepine intermediates
JPH0227994B2 (da)	1990-06-20
US4640930A (en)	1987-02-03	Naphtho(1,8-bc)-1,5-thiazocinones
US6380388B1 (en)	2002-04-30	1,3-oxathiolan-5-ones useful in the production of antiviral nucleoside analogues
KR0142428B1 (ko)	1998-07-01	1,4-가교된 시클로헥산 카르복실산 유도체의 제조방법
US5705638A (en)	1998-01-06	Process for preparing optically active 3-hydroxy-1,5-benzothiazepine derivative and intermediate therefor
US20040236103A1 (en)	2004-11-25	Methods for producing oxirane carboxylic acids and derivatives thereof
JPH0573749B2 (da)	1993-10-15
SK114195A3 (en)	1996-06-05	Preparing method of 3-hydroxy-5-£2-(dimethyl-ami-no)-ethyl\|-2,3-dihydro-2-(4- -metoxyphenyl)-1,5-benzothiazepin-4(5h)one and its salts
JPH0533705B2 (da)	1993-05-20