DD215547A5 - Verfahren zur herstellung von 6,11-dihydro-dibenzo-(b,e)-thiepin-11-n-alkyl-norscopinether - Google Patents

Verfahren zur herstellung von 6,11-dihydro-dibenzo-(b,e)-thiepin-11-n-alkyl-norscopinether Download PDF

Info

Publication number: DD215547A5
Authority: DD; German Democratic Republic
Prior art keywords: dihydro; preparation; compounds; dibenzo; thiepin
Prior art date: 1982-03-26

Application number

DD83259313A

Other languages

German (de)

English (en)

Inventor

Banholzer

Bauer

Original Assignee

Boehringer Ingelheim Kg

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.)

1982-03-26

Filing date

1983-03-24

Publication date

1984-11-14

1983-03-24 Application filed by Boehringer Ingelheim Kg filed Critical Boehringer Ingelheim Kg

1984-11-14 Publication of DD215547A5 publication Critical patent/DD215547A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 14
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 10
230000000694 effects Effects 0.000 abstract description 5
230000001813 broncholytic effect Effects 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 4
238000005956 quaternization reaction Methods 0.000 abstract description 3
125000004432 carbon atom Chemical group C* 0.000 abstract description 2
239000007795 chemical reaction product Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000000443 aerosol Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000029058 respiratory gaseous exchange Effects 0.000 description 6
238000012360 testing method Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 5
229960004373 acetylcholine Drugs 0.000 description 5
210000000056 organ Anatomy 0.000 description 5
241000282472 Canis lupus familiaris Species 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000000812 cholinergic antagonist Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
241000700199 Cavia porcellus Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 description 3
208000005392 Spasm Diseases 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
229960001340 histamine Drugs 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
FIMXSEMBHGTNKT-UPGAHCIJSA-N scopine Chemical compound C([C@@H]1N2C)C(O)C[C@@H]2[C@@H]2[C@H]1O2 FIMXSEMBHGTNKT-UPGAHCIJSA-N 0.000 description 3
230000002048 spasmolytic effect Effects 0.000 description 3
238000009423 ventilation Methods 0.000 description 3
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
208000009079 Bronchial Spasm Diseases 0.000 description 2
208000014181 Bronchial disease Diseases 0.000 description 2
206010006482 Bronchospasm Diseases 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
208000007101 Muscle Cramp Diseases 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
230000000572 bronchospasmolytic effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229960001361 ipratropium bromide Drugs 0.000 description 2
KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 2
239000000203 mixture Substances 0.000 description 2
210000000664 rectum Anatomy 0.000 description 2
150000003839 salts Chemical group 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
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 1
102100040141 Aminopeptidase O Human genes 0.000 description 1
108050008333 Aminopeptidase O Proteins 0.000 description 1
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
229930003347 Atropine Natural products 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
239000004964 aerogel Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000001078 anti-cholinergic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
229960000396 atropine Drugs 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000037396 body weight Effects 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
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
229960000520 diphenhydramine Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
206010013781 dry mouth Diseases 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000013401 experimental design Methods 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000012886 linear function Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
230000003533 narcotic effect Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000012887 quadratic function Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000003506 spasmogen Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/08—Diarylmethoxy radicals

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrane Compounds (AREA)

DD83259313A 1982-03-26 1983-03-24 Verfahren zur herstellung von 6,11-dihydro-dibenzo-(b,e)-thiepin-11-n-alkyl-norscopinether DD215547A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19823211185 DE3211185A1 (de)	1982-03-26	1982-03-26	Neue quartaere 6,11-dihydro-dibenzo-(b,e)-thiepin-11-n-alkyl- norscopinether und verfahren zu deren herstellung

Publications (1)

Publication Number	Publication Date
DD215547A5 true DD215547A5 (de)	1984-11-14

Family

ID=6159392

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD83259313A DD215547A5 (de)	1982-03-26	1983-03-24	Verfahren zur herstellung von 6,11-dihydro-dibenzo-(b,e)-thiepin-11-n-alkyl-norscopinether
DD83249134A DD210276A5 (de)	1982-03-26	1983-03-24	Verfahren zur herstellung von 6,11-dihydro-dibenzo-(b,e)-thiepin-11-n-alkylnorscopinether

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD83249134A DD210276A5 (de)	1982-03-26	1983-03-24	Verfahren zur herstellung von 6,11-dihydro-dibenzo-(b,e)-thiepin-11-n-alkylnorscopinether

Country Status (25)

Country	Link
US (1)	US4608377A (no)
EP (1)	EP0090195B1 (no)
JP (1)	JPS58174380A (no)
KR (1)	KR900004143B1 (no)
AT (1)	ATE16591T1 (no)
AU (1)	AU554262B2 (no)
CA (1)	CA1254564A (no)
CS (2)	CS236790B2 (no)
DD (2)	DD215547A5 (no)
DE (2)	DE3211185A1 (no)
DK (1)	DK164703C (no)
ES (2)	ES8402290A1 (no)
FI (1)	FI73995C (no)
GR (1)	GR77437B (no)
HU (1)	HU189675B (no)
IE (1)	IE55110B1 (no)
IL (1)	IL68230A0 (no)
NO (1)	NO158741C (no)
NZ (1)	NZ203696A (no)
PH (1)	PH20502A (no)
PL (1)	PL138982B1 (no)
PT (1)	PT76420B (no)
SU (1)	SU1144618A3 (no)
YU (1)	YU42847B (no)
ZA (1)	ZA832135B (no)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3215493A1 (de) *	1982-04-26	1983-11-03	Boehringer Ingelheim KG, 6507 Ingelheim	Neue zwischenprodukte, verfahren zu ihrer herstellung und ihre verwendung
DE3215490A1 (de) *	1982-04-26	1983-11-03	Boehringer Ingelheim KG, 6507 Ingelheim	Neues vorprodukt, verfahren zu seiner herstellung und seine verwendung
CN1426401A (zh) *	2000-04-27	2003-06-25	贝林格尔英格海姆法玛公司	新的长效倍他米美类药物(betamimetics)其制备方法,及其作为药物组合物的用途
CA2395653C (en) *	2000-10-12	2006-05-09	Boehringer Ingelheim Pharma Kg	New inhalable powder containing tiotropium
US6908928B2 (en)	2000-10-12	2005-06-21	Bi Pharma Kg.	Crystalline tiotropium bromide monohydrate, processes for the preparation thereof, and pharmaceutical compositions
US6852728B2 (en)	2000-10-14	2005-02-08	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Anticholinergics, processes for preparing them, and pharmaceutical compositions containing them
US6706726B2 (en)	2000-10-14	2004-03-16	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Anticholinergics which may be used as medicaments as well as processes for preparing them
US20020137764A1 (en) *	2000-10-31	2002-09-26	Karin Drechsel	Inhalable formulation of a solution containing a tiotropium salt
US20020151541A1 (en) *	2000-10-31	2002-10-17	Michel Pairet	Pharmaceutical compositions containing tiotropium salts and antihistamines and their use
DE10062712A1 (de) *	2000-12-15	2002-06-20	Boehringer Ingelheim Pharma	Neue Arzneimittelkompositionen auf der Basis von Anticholinergika und Corticosteroiden
US20020111363A1 (en) *	2000-10-31	2002-08-15	Karin Drechsel	Inhalable formulation of a solution containing a tiotropium salt
US7776315B2 (en) *	2000-10-31	2010-08-17	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Pharmaceutical compositions based on anticholinergics and additional active ingredients
US20020193392A1 (en) *	2000-11-13	2002-12-19	Christel Schmelzer	Pharmaceutical compositions based on tiotropium salts of salts of salmeterol
US20100310477A1 (en) *	2000-11-28	2010-12-09	Boehringer Ingelheim Pharma Gmbh & Co. Kg.	Pharmaceutical compositions based on anticholingerics and additional active ingredients
US20030013675A1 (en) *	2001-05-25	2003-01-16	Boehringer Ingelheim Pharma Kg	Combination of an adenosine A2A-receptor agonist and tiotropium or a derivative thereof for treating obstructive airways and other inflammatory diseases
US20030070679A1 (en) *	2001-06-01	2003-04-17	Boehringer Ingelheim Pharma Kg	Capsules containing inhalable tiotropium
US20030018019A1 (en) *	2001-06-23	2003-01-23	Boehringer Ingelheim Pharma Kg	Pharmaceutical compositions based on anticholinergics, corticosteroids and betamimetics
DE10141377A1 (de) *	2001-08-23	2003-03-13	Boehringer Ingelheim Pharma	Aufstreuverfahren zur Herstellung von Pulverformulierungen
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1982
- 1982-03-26 DE DE19823211185 patent/DE3211185A1/de not_active Withdrawn
1983
- 1983-02-25 DK DK094783A patent/DK164703C/da not_active IP Right Cessation
- 1983-03-04 EP EP83102109A patent/EP0090195B1/de not_active Expired
- 1983-03-04 DE DE8383102109T patent/DE3361261D1/de not_active Expired
- 1983-03-04 AT AT83102109T patent/ATE16591T1/de active
- 1983-03-11 PH PH28632A patent/PH20502A/en unknown
- 1983-03-21 PT PT76420A patent/PT76420B/pt not_active IP Right Cessation
- 1983-03-22 SU SU833566494A patent/SU1144618A3/ru active
- 1983-03-23 FI FI830979A patent/FI73995C/fi not_active IP Right Cessation
- 1983-03-23 GR GR70859A patent/GR77437B/el unknown
- 1983-03-23 YU YU707/83A patent/YU42847B/xx unknown
- 1983-03-24 CS CS832040A patent/CS236790B2/cs unknown
- 1983-03-24 PL PL1983241175A patent/PL138982B1/pl unknown
- 1983-03-24 DD DD83259313A patent/DD215547A5/de not_active IP Right Cessation
- 1983-03-24 KR KR1019830001184A patent/KR900004143B1/ko not_active IP Right Cessation
- 1983-03-24 IL IL68230A patent/IL68230A0/xx not_active IP Right Cessation
- 1983-03-24 DD DD83249134A patent/DD210276A5/de not_active IP Right Cessation
- 1983-03-25 ZA ZA832135A patent/ZA832135B/xx unknown
- 1983-03-25 IE IE671/83A patent/IE55110B1/en not_active IP Right Cessation
- 1983-03-25 CA CA000424451A patent/CA1254564A/en not_active Expired
- 1983-03-25 ES ES520985A patent/ES8402290A1/es not_active Expired
- 1983-03-25 NZ NZ203696A patent/NZ203696A/en unknown
- 1983-03-25 JP JP58050268A patent/JPS58174380A/ja active Granted
- 1983-03-25 NO NO831084A patent/NO158741C/no unknown
- 1983-03-25 AU AU12866/83A patent/AU554262B2/en not_active Ceased
- 1983-03-25 ES ES520988A patent/ES8401971A1/es not_active Expired
- 1983-03-25 HU HU831023A patent/HU189675B/hu not_active IP Right Cessation
1984
- 1984-06-25 US US06/623,963 patent/US4608377A/en not_active Expired - Fee Related
1991
- 1991-12-27 CS CS914105A patent/CS410591A3/cs unknown

Also Published As

Publication number	Publication date
ES520988A0 (es)	1984-01-01
FI830979A0 (fi)	1983-03-23
FI830979L (fi)	1983-09-27
NZ203696A (en)	1985-08-16
IL68230A0 (en)	1983-06-15
HU189675B (en)	1986-07-28
DK164703B (da)	1992-08-03
PT76420A (de)	1983-04-01
JPS58174380A (ja)	1983-10-13
DE3361261D1 (en)	1986-01-02
CS236790B2 (en)	1985-05-15
PL138982B1 (en)	1986-11-29
DK94783A (da)	1983-09-27
FI73995B (fi)	1987-08-31
PH20502A (en)	1987-01-21
AU1286683A (en)	1983-09-29
DE3211185A1 (de)	1983-09-29
EP0090195B1 (de)	1985-11-21
NO831084L (no)	1983-09-27
FI73995C (fi)	1987-12-10
YU70783A (en)	1985-12-31
ZA832135B (en)	1984-11-28
DK164703C (da)	1992-12-21
DD210276A5 (de)	1984-06-06
ES520985A0 (es)	1984-01-16
PT76420B (pt)	1986-02-04
YU42847B (en)	1988-12-31
DK94783D0 (da)	1983-02-25
PL241175A1 (en)	1984-01-30
ES8402290A1 (es)	1984-01-16
NO158741C (no)	1988-10-26
SU1144618A3 (ru)	1985-03-07
CA1254564A (en)	1989-05-23
GR77437B (no)	1984-09-14
KR900004143B1 (ko)	1990-06-16
US4608377A (en)	1986-08-26
CS410591A3 (en)	1992-06-17
NO158741B (no)	1988-07-18
EP0090195A1 (de)	1983-10-05
ATE16591T1 (de)	1985-12-15
IE55110B1 (en)	1990-06-06
ES8401971A1 (es)	1984-01-01
IE830671L (en)	1983-09-26
KR840004106A (ko)	1984-10-06
AU554262B2 (en)	1986-08-14
JPH0358347B2 (no)	1991-09-05

Publication	Publication Date	Title
DD215547A5 (de)	1984-11-14	Verfahren zur herstellung von 6,11-dihydro-dibenzo-(b,e)-thiepin-11-n-alkyl-norscopinether
Clarke et al.	1973	Compounds affecting the central nervous system. 4. 3. beta.-phenyltropane-2-carboxylic esters and analogs
DE69733353T2 (de)	2006-02-02	Immunsuppressive wirkstoffe und verfahren
DE2203373B2 (de)	1977-08-11	Neue 2- eckige klammer auf (2- alkylbenzofuran-3-yl)-methyl eckige klammer zu -delta hoch 2 -imidazoline
DE10046029A1 (de)	2002-03-28	Indazole
EP0043940B1 (de)	1984-09-12	3,1-Benzoxazin-2-one, ihre Herstellung und Verwendung
DE60003911T2 (de)	2004-05-27	Heteroaryl-diazacycloalkane, ihre herstellung und verwendung
DD249480A5 (de)	1987-09-09	3-amino-dihydro-(1)-benzopyrane und benzothiopyrane
DE60016786T2 (de)	2005-12-22	Bicyclische vasopressin-agoniste
DE2211738C3 (de)	1974-09-12	(2,4-Diallylamino-6-pyrimidinyl)piperazine
DD202567A5 (de)	1983-09-21	Verfahren zur herstellung von piperazinderivaten
DE2433863C3 (de)	1982-04-29	1-Amidino-3-phenyl-harnstoffe, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende therapeutische Zubereitungen
DE2221758A1 (de)	1972-11-23	Yohimbinderivate,Verfahren zu ihrer Herstellung und ihre Verwendung
DE2821584A1 (de)	1978-11-30	Neue, pharmazeutisch wirksame verbindungen, verfahren zu ihrer herstellung und arzneimittel
DE2247374A1 (de)	1973-04-05	Substituierte isochinoline und verfahren zu deren herstellung
DE2627080A1 (de)	1977-01-20	Neues naphthacenderivat, dessen herstellung und dieses enthaltende zusammensetzungen
AT345807B (de)	1978-10-10	Verfahren zur herstellung neuer substituierter arylalkylamine und deren salze
DD215540A5 (de)	1984-11-14	Verfahren zur herstellung von benzazepinderivaten
CH639107A5 (de)	1983-10-31	Neue acylderivate des hellebrigenins.
AT345810B (de)	1978-10-10	Verfahren zur herstellung neuer substituierter arylalkylamine und deren salze
AT345808B (de)	1978-10-10	Verfahren zur herstellung neuer substituierter arylalkylamine und deren salze
AT236951B (de)	1964-11-25	Verfahren zur Herstellung von neuen Triazolidinen
AT238183B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
DE3151780A1 (de)	1982-09-30	Tetrahydro-1,2,4-oxadiazin-5-onderivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und die verwendung der ersteren
EP0462150A1 (de)	1991-12-27	Neue aryloxy-alkylamine, deren herstellung und diese enthaltende arzneimittel.

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