HRP20000473A2 - Novel process for preparing a ketamine - Google Patents

Novel process for preparing a ketamine Download PDF

Info

Publication number: HRP20000473A2
Authority: HR; Croatia
Prior art keywords: sertraline; cis; mixture; monomethylamine; solvent
Prior art date: 1998-01-16

Application number

HR20000473A

Other languages

English (en)

Croatian (hr)

Inventor

Juan Carlos Colberg

David Michael Pfisterer

Geraldine Patricia Taber

Original Assignee

Pfizer Prod 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.)

1998-01-16

Filing date

2000-07-14

Publication date

2001-04-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22102365&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=HRP20000473(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2000-07-14 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2001-04-30 Publication of HRP20000473A2 publication Critical patent/HRP20000473A2/hr

Links

238000004519 manufacturing process Methods 0.000 title description 5
YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 title 1
229960003299 ketamine Drugs 0.000 title 1
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 83
VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 claims description 76
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 59
238000000034 method Methods 0.000 claims description 56
239000000203 mixture Substances 0.000 claims description 55
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
229960002073 sertraline Drugs 0.000 claims description 48
239000002904 solvent Substances 0.000 claims description 38
238000006243 chemical reaction Methods 0.000 claims description 37
150000004658 ketimines Chemical class 0.000 claims description 24
229910052799 carbon Inorganic materials 0.000 claims description 22
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
239000003054 catalyst Substances 0.000 claims description 17
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 16
MGBVAZJASCWJGJ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-n-methyl-3,4-dihydro-2h-naphthalen-1-imine Chemical compound C12=CC=CC=C2C(=NC)CCC1C1=CC=C(Cl)C(Cl)=C1 MGBVAZJASCWJGJ-UHFFFAOYSA-N 0.000 claims description 14
JGMBHJNMQVKDMW-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C2=CC=CC=C2C(=O)CC1 JGMBHJNMQVKDMW-UHFFFAOYSA-N 0.000 claims description 12
238000005984 hydrogenation reaction Methods 0.000 claims description 12
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 10
150000001298 alcohols Chemical class 0.000 claims description 9
VGKDLMBJGBXTGI-SJKOYZFVSA-N (1r,4r)-4-(3,4-dichlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1([C@H]2CC[C@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJKOYZFVSA-N 0.000 claims description 8
238000009835 boiling Methods 0.000 claims description 8
230000001476 alcoholic effect Effects 0.000 claims description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
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 4
150000001875 compounds Chemical class 0.000 claims description 4
235000019445 benzyl alcohol Nutrition 0.000 claims description 3
238000011065 in-situ storage Methods 0.000 claims description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 6
239000000463 material Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 description 18
238000001914 filtration Methods 0.000 description 18
239000000047 product Substances 0.000 description 18
229910052739 hydrogen Inorganic materials 0.000 description 15
239000001257 hydrogen Substances 0.000 description 15
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 14
238000005755 formation reaction Methods 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
150000002466 imines Chemical class 0.000 description 10
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical class [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 10
239000006227 byproduct Substances 0.000 description 9
229910000019 calcium carbonate Inorganic materials 0.000 description 7
235000010216 calcium carbonate Nutrition 0.000 description 7
239000012458 free base Substances 0.000 description 7
239000002808 molecular sieve Substances 0.000 description 7
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
238000006482 condensation reaction Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000006268 reductive amination reaction Methods 0.000 description 5
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 5
MGBVAZJASCWJGJ-LBPRGKRZSA-N (4s)-4-(3,4-dichlorophenyl)-n-methyl-3,4-dihydro-2h-naphthalen-1-imine Chemical compound C1([C@@H]2CCC(C3=CC=CC=C32)=NC)=CC=C(Cl)C(Cl)=C1 MGBVAZJASCWJGJ-LBPRGKRZSA-N 0.000 description 4
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 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
238000002955 isolation Methods 0.000 description 4
-1 ketimine compound Chemical class 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000005292 vacuum distillation Methods 0.000 description 4
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 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
VGKDLMBJGBXTGI-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C12=CC=CC=C2C(NC)CCC1C1=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-UHFFFAOYSA-N 0.000 description 3
GLQPTZAAUROJMO-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)benzaldehyde Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC=C(C=O)C=C1 GLQPTZAAUROJMO-UHFFFAOYSA-N 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
229960002510 mandelic acid Drugs 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229960003660 sertraline hydrochloride Drugs 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
238000004042 decolorization Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
GPBNEZFEHRXEKC-UHFFFAOYSA-N methanamine oxygen(2-) titanium(4+) hydrochloride Chemical compound Cl.CN.[O-2].[O-2].[Ti+4] GPBNEZFEHRXEKC-UHFFFAOYSA-N 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000007787 solid Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
IXLVUUFUDRJUSL-RPBOFIJWSA-N 5-[[4-(3-acetamidophenyl)phenyl]methyl]-n-[(1s,2r)-2-phenylcyclopropyl]-1,3-oxazole-4-carboxamide Chemical compound CC(=O)NC1=CC=CC(C=2C=CC(CC3=C(N=CO3)C(=O)N[C@@H]3[C@H](C3)C=3C=CC=CC=3)=CC=2)=C1 IXLVUUFUDRJUSL-RPBOFIJWSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
238000003556 assay Methods 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000035425 carbon utilization Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000011148 porous material Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000004321 preservation Methods 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
229940020965 zoloft Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Cephalosporin Compounds (AREA)
Steroid Compounds (AREA)

HR20000473A 1998-01-16 2000-07-14 Novel process for preparing a ketamine HRP20000473A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7160098P	1998-01-16	1998-01-16
PCT/IB1998/001619 WO1999036394A1 (en)	1998-01-16	1998-10-15	Novel process for preparing a ketimine

Publications (1)

Publication Number	Publication Date
HRP20000473A2 true HRP20000473A2 (en)	2001-04-30

Family

ID=22102365

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20000473A HRP20000473A2 (en)	1998-01-16	2000-07-14	Novel process for preparing a ketamine

Country Status (48)

Country	Link
US (1)	US6232500B1 (es)
EP (1)	EP1047666B1 (es)
JP (1)	JP3533179B2 (es)
KR (1)	KR100362788B1 (es)
CN (1)	CN1121381C (es)
AP (1)	AP956A (es)
AR (1)	AR016168A1 (es)
AT (1)	ATE231121T1 (es)
AU (1)	AU747861B2 (es)
BG (2)	BG64647B1 (es)
BR (1)	BR9814248A (es)
CA (1)	CA2315761C (es)
CO (1)	CO5040154A1 (es)
CZ (1)	CZ20002594A3 (es)
DE (1)	DE69810815T2 (es)
DK (1)	DK1047666T3 (es)
DZ (1)	DZ2705A1 (es)
EA (1)	EA004952B1 (es)
EG (1)	EG21515A (es)
ES (1)	ES2186226T3 (es)
GT (1)	GT199800176A (es)
HK (1)	HK1032039A1 (es)
HN (1)	HN1998000167A (es)
HR (1)	HRP20000473A2 (es)
HU (1)	HUP0101253A3 (es)
ID (1)	ID24971A (es)
IL (2)	IL136888A0 (es)
IN (1)	IN191358B (es)
IS (1)	IS5538A (es)
MA (1)	MA24744A1 (es)
MY (1)	MY132956A (es)
NO (1)	NO20003625L (es)
NZ (1)	NZ505027A (es)
OA (1)	OA11439A (es)
PA (1)	PA8461901A1 (es)
PE (1)	PE20000171A1 (es)
PL (1)	PL192489B1 (es)
PT (1)	PT1047666E (es)
RS (1)	RS49773B (es)
SI (1)	SI1047666T1 (es)
SK (1)	SK10182000A3 (es)
TN (1)	TNSN99004A1 (es)
TR (1)	TR200002065T2 (es)
TW (1)	TW505624B (es)
UA (1)	UA55504C2 (es)
UY (1)	UY25348A1 (es)
WO (1)	WO1999036394A1 (es)
ZA (1)	ZA99278B (es)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU226423B1 (en) *	1998-05-05	2008-12-29	Egis Gyogyszergyar Nyrt	Process for producing a 1(2h)-naphtalene-1-ylidene derivative
CA2346900A1 (en) *	1998-10-30	2000-05-11	Ciba Specialty Chemicals Holding Inc.	Method of producing ketimines
EP1632474A1 (en) *	1998-11-27	2006-03-08	Teva Pharmaceutical Industries Ltd.	Sertraline hydrochloride polymorphs
IN185109B (es) *	1999-09-01	2000-11-18	Torrent Pharmaceuticals Ltd
CN1250522C (zh) *	1999-11-16	2006-04-12	西巴特殊化学品控股有限公司	制备酮亚胺的方法
JP2003514795A (ja) *	1999-11-16	2003-04-22	チバスペシャルティケミカルズホールディングインコーポレーテッド	ケトイミンの調製方法
IN187170B (es)	2000-01-04	2002-02-23	Sun Pharmaceutical Ind Ltd
AU4363401A (en) *	2000-03-14	2001-09-24	Teva Pharma	Novel process for preparing (+)-cis-sertraline
WO2002096860A1 (en) *	2001-05-31	2002-12-05	Orion Corporation Fermion	Process for preparing sertraline intermediates
US6723878B2 (en)	2001-06-15	2004-04-20	Orion Corporation Fermion	Method for preparing sertraline
KR20030061474A (ko) *	2002-01-14	2003-07-22	한미약품 주식회사	서트랄린 제조용 중간체로서 사용되는 시스-라세메이트화합물의 개선된 제조방법
US20070260090A1 (en)	2005-06-03	2007-11-08	Hetero Drugs Limited	Highly Steroselective Synthesis of Sertraline

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4536518A (en)	1979-11-01	1985-08-20	Pfizer Inc.	Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine
US4855500A (en)	1988-05-04	1989-08-08	Pfizer Inc.	Process for preparing a ketimine
HU226424B1 (en)	1998-05-05	2008-12-29	Egis Gyogyszergyar Nyrt	Process for producing enantiomer mixture for preparation of sertraline

1998
- 1998-06-24 IN IN8499DE1998 patent/IN191358B/en unknown
- 1998-10-15 BR BR9814248-8A patent/BR9814248A/pt not_active Application Discontinuation
- 1998-10-15 HU HU0101253A patent/HUP0101253A3/hu unknown
- 1998-10-15 KR KR1020007007730A patent/KR100362788B1/ko not_active IP Right Cessation
- 1998-10-15 PL PL341648A patent/PL192489B1/pl not_active IP Right Cessation
- 1998-10-15 EP EP98945508A patent/EP1047666B1/en not_active Revoked
- 1998-10-15 UA UA2000074225A patent/UA55504C2/uk unknown
- 1998-10-15 DE DE69810815T patent/DE69810815T2/de not_active Revoked
- 1998-10-15 DK DK98945508T patent/DK1047666T3/da active
- 1998-10-15 TR TR2000/02065T patent/TR200002065T2/xx unknown
- 1998-10-15 CZ CZ20002594A patent/CZ20002594A3/cs unknown
- 1998-10-15 US US09/380,562 patent/US6232500B1/en not_active Expired - Fee Related
- 1998-10-15 SI SI9830331T patent/SI1047666T1/xx unknown
- 1998-10-15 NZ NZ505027A patent/NZ505027A/xx unknown
- 1998-10-15 ID IDW20001367A patent/ID24971A/id unknown
- 1998-10-15 SK SK1018-2000A patent/SK10182000A3/sk unknown
- 1998-10-15 JP JP2000540112A patent/JP3533179B2/ja not_active Expired - Fee Related
- 1998-10-15 WO PCT/IB1998/001619 patent/WO1999036394A1/en not_active Application Discontinuation
- 1998-10-15 IL IL13688898A patent/IL136888A0/xx active IP Right Grant
- 1998-10-15 CN CN98813087A patent/CN1121381C/zh not_active Expired - Fee Related
- 1998-10-15 ES ES98945508T patent/ES2186226T3/es not_active Expired - Lifetime
- 1998-10-15 CA CA002315761A patent/CA2315761C/en not_active Expired - Fee Related
- 1998-10-15 EA EA200000661A patent/EA004952B1/ru not_active IP Right Cessation
- 1998-10-15 RS YUP-443/00A patent/RS49773B/sr unknown
- 1998-10-15 AT AT98945508T patent/ATE231121T1/de not_active IP Right Cessation
- 1998-10-15 PT PT98945508T patent/PT1047666E/pt unknown
- 1998-10-15 AU AU92786/98A patent/AU747861B2/en not_active Ceased
- 1998-10-22 PA PA19988461901A patent/PA8461901A1/es unknown
- 1998-10-26 HN HN1998000167A patent/HN1998000167A/es unknown
- 1998-11-09 GT GT199800176A patent/GT199800176A/es unknown
- 1998-11-30 CO CO98070715A patent/CO5040154A1/es unknown
1999
- 1999-01-11 PE PE1999000023A patent/PE20000171A1/es not_active Application Discontinuation
- 1999-01-11 EG EG2799A patent/EG21515A/xx active
- 1999-01-13 DZ DZ990006A patent/DZ2705A1/xx active
- 1999-01-13 MA MA25427A patent/MA24744A1/fr unknown
- 1999-01-13 MY MYPI99000116A patent/MY132956A/en unknown
- 1999-01-13 TW TW088100478A patent/TW505624B/zh not_active IP Right Cessation
- 1999-01-13 TN TNTNSN99004A patent/TNSN99004A1/fr unknown
- 1999-01-13 UY UY25348A patent/UY25348A1/es not_active IP Right Cessation
- 1999-01-14 AP APAP/P/1999/001441A patent/AP956A/en active
- 1999-01-15 AR ARP990100129A patent/AR016168A1/es active IP Right Grant
- 1999-01-15 ZA ZA9900278A patent/ZA99278B/xx unknown
2000
- 2000-06-16 IS IS5538A patent/IS5538A/is unknown
- 2000-06-19 IL IL136888A patent/IL136888A/en not_active IP Right Cessation
- 2000-06-30 OA OA1200000193A patent/OA11439A/en unknown
- 2000-07-14 HR HR20000473A patent/HRP20000473A2/hr not_active Application Discontinuation
- 2000-07-14 NO NO20003625A patent/NO20003625L/no not_active Application Discontinuation
- 2000-08-07 BG BG108878A patent/BG64647B1/bg unknown
- 2000-08-07 BG BG104669A patent/BG64621B1/bg unknown
2001
- 2001-04-10 HK HK01102504A patent/HK1032039A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU747861B2 (en)	2002-05-23
HN1998000167A (es)	1999-02-09
RS49773B (sr)	2008-06-05
CZ20002594A3 (cs)	2001-12-12
HK1032039A1 (en)	2001-07-06
IL136888A (en)	2006-12-10
AP956A (en)	2001-04-06
TNSN99004A1 (fr)	2005-11-10
EA004952B1 (ru)	2004-10-28
HUP0101253A3 (en)	2002-06-28
CO5040154A1 (es)	2001-05-29
OA11439A (en)	2004-04-26
JP2002509132A (ja)	2002-03-26
EP1047666B1 (en)	2003-01-15
EA200000661A1 (ru)	2000-12-25
NO20003625D0 (no)	2000-07-14
DZ2705A1 (fr)	2003-09-01
ZA99278B (en)	2000-07-17
PL192489B1 (pl)	2006-10-31
DE69810815D1 (de)	2003-02-20
DK1047666T3 (da)	2003-02-24
TW505624B (en)	2002-10-11
IS5538A (is)	2000-06-16
IN191358B (es)	2003-11-29
PL341648A1 (en)	2001-04-23
HUP0101253A2 (hu)	2002-05-29
IL136888A0 (en)	2001-06-14
YU44300A (sh)	2002-09-19
CN1285819A (zh)	2001-02-28
CA2315761A1 (en)	1999-07-22
TR200002065T2 (tr)	2000-11-21
CA2315761C (en)	2004-08-31
BG64621B1 (bg)	2005-09-30
AP9901441A0 (en)	1999-03-31
KR100362788B1 (ko)	2002-11-29
US6232500B1 (en)	2001-05-15
EP1047666A1 (en)	2000-11-02
NZ505027A (en)	2002-08-28
ATE231121T1 (de)	2003-02-15
SK10182000A3 (sk)	2002-06-04
EG21515A (en)	2001-11-28
MA24744A1 (fr)	1999-10-01
MY132956A (en)	2007-10-31
BG104669A (en)	2001-04-30
WO1999036394A1 (en)	1999-07-22
KR20010034117A (ko)	2001-04-25
PE20000171A1 (es)	2000-03-09
JP3533179B2 (ja)	2004-05-31
PA8461901A1 (es)	2000-05-24
SI1047666T1 (en)	2003-04-30
DE69810815T2 (de)	2003-08-07
ID24971A (id)	2000-08-31
BR9814248A (pt)	2000-10-10
CN1121381C (zh)	2003-09-17
UA55504C2 (uk)	2003-04-15
UY25348A1 (es)	1999-09-27
AR016168A1 (es)	2001-06-20
AU9278698A (en)	1999-08-02
ES2186226T3 (es)	2003-05-01
NO20003625L (no)	2000-09-13
GT199800176A (es)	1998-11-09
BG64647B1 (bg)	2005-10-31
PT1047666E (pt)	2003-03-31

Legal Events

Date	Code	Title
2001-04-30	A1OB	Publication of a patent application
2001-06-12	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2008-11-18	OBST	Application withdrawn

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US6900355B2 (en)	2005-05-31	Process for the cis-selective catalytic hydrogenation of cyclohexylidenamines
WO2006067808A1 (en)	2006-06-29	An improved process for production of intermediate of antidepressant agent
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JPH07291903A (ja)	1995-11-07	Ｎ，ｎ−ジ置換ベンジルアミンの製造方法
MXPA00005680A (es)	2002-07-25	Procedimiento para preparar sertralina a partir de tretalona quiral
EP2476665A1 (en)	2012-07-18	Process for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)- 3-phenyl propylamine and its salts starting from a novel intermediate